|
|
|
|
LEADER |
06866cam a22008412 4500 |
001 |
0-1651097984 |
003 |
DE-627 |
005 |
20230426024225.0 |
007 |
cr uuu---uuuuu |
008 |
111216s2012 ja |||||o 00| ||eng c |
020 |
|
|
|a 9784431540434
|9 978-4-431-54043-4
|
024 |
7 |
|
|a 10.1007/978-4-431-54043-4
|2 doi
|
035 |
|
|
|a (DE-627)1651097984
|
035 |
|
|
|a (DE-576)355115832
|
035 |
|
|
|a (DE-599)BSZ355115832
|
035 |
|
|
|a (OCoLC)838808974
|
035 |
|
|
|a (OCoLC)772669817
|
035 |
|
|
|a (DE-He213)978-4-431-54043-4
|
040 |
|
|
|a DE-627
|b ger
|c DE-627
|e rakwb
|
041 |
|
|
|a eng
|
044 |
|
|
|c XB-JP
|
050 |
|
0 |
|a QD241-441
|
050 |
|
0 |
|a QD181.S1 .I889 2012
|
082 |
0 |
|
|a 547
|
082 |
0 |
|
|a 546.723
|
084 |
|
|
|a PSB
|2 bicssc
|
084 |
|
|
|a SCI013040
|2 bisacsh
|
084 |
|
|
|a SCI007000
|2 bisacsh
|
100 |
1 |
|
|a Inuki, Shinsuke
|4 aut
|
245 |
1 |
0 |
|a Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds
|c by Shinsuke Inuki
|
264 |
|
1 |
|a Tokyo
|b Springer Tokyo
|c 2012
|
300 |
|
|
|a Online-Ressource (XVI, 106p. 66 illus, digital)
|
336 |
|
|
|a Text
|b txt
|2 rdacontent
|
337 |
|
|
|a Computermedien
|b c
|2 rdamedia
|
338 |
|
|
|a Online-Ressource
|b cr
|2 rdacarrier
|
490 |
0 |
|
|a Springer Theses
|
490 |
0 |
|
|a SpringerLink
|a Bücher
|
500 |
|
|
|a Description based upon print version of record
|
505 |
8 |
0 |
|a Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds; Supervisors' Foreword; Acknowledgments; Contents; 1 Introduction; Abstract; References; Part ITotal Synthesis of Pachastrissamine (Jaspine B); 2 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Bromoallenes; Abstract; 2.1…Experimental Section; 2.1.1 General Methods; 2.1.2 tert-Butyl (R)-4-[(R)-3-Bromopropa-1,2-dienyl]-2, 2-dimethyloxazolidine-3-carboxylate (12a); 2.1.3 N-[(2R,4R)-5-Bromo-1-hydroxypenta-3,4-dien-2-yl] benzamide (9a)
|
505 |
8 |
0 |
|a 2.1.4 (3aS,6aS)-6-Methylene-2-phenyl-3a,4,6,6a -tetrahydrofuro[3,4-d]oxazole (8)2.1.5 (R)-N-[5-(Methoxymethyl)-2,3-dihydrofuran-3-yl] benzamide (13a); 2.1.6 (R)-N-{5-[(2,2,2-Trifluoroethoxy)methyl] -2,3-dihydrofuran-3-yl}benzamide (13b); 2.1.7 N-(5-Methylfuran-3-yl)benzamide (14); 2.1.8 tert-Butyl (R)-4-[(S)-3-Bromopropa-1,2-dienyl]-2, 2-dimethyloxazolidine-3-carboxylate (12b); 2.1.9 N-[(2R,4S)-5-Bromo-1-hydroxypenta -3,4-dien-2-yl]benzamide (9b); 2.1.10 [(3aS,6S,6aS)-2-Phenyl-3a,4,6,6a-tetrahydrofuro [3,4-d]oxazol-6-yl]methanol (15)
|
505 |
8 |
0 |
|a 2.1.11 (3aS,6S,6aS)-2-Phenyl-6-tetradecyl-3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (16)2.1.12 (3aS,6S,6aS)-2-Phenyl-6-(3-phenylpropyl) -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17a); 2.1.13 (3aS,6S,6aS)-6-Ethyl-2-phenyl-3a,4,6, 6a-tetrahydrofuro[3,4-d]oxazole (17b); 2.1.14 (3aS,6S,6aS)-6-Isobutyl-2-phenyl-3a,4,6, 6a-tetrahydrofuro[3,4-d]oxazole (17c); 2.1.15 (3aS,6S,6aS)-6-(2-Methylallyl)-2-phenyl -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17d); 2.1.16 (1S,4S,7S)-5-(4-Phenylhepta-1,6-dien-4-yl) -2-oxa-5-azabicyclo[2.2.1]heptan-7-ol (18)
|
505 |
8 |
0 |
|a 2.1.17 (3aS,6S,6aS)-6-(But-3-enyl)-2-phenyl -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17e)References; 3 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Propargyl Chlorides and Carbonates; Abstract; 3.1…Experimental Section; 3.1.1 General Methods; 3.1.2 tert-Butyl (S)-4-[(S)-1-Hydroxyhexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-6); 3.1.3 tert-Butyl (S)-4-[(R)-1-Hydroxyhexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-6); 3.1.4 tert-Butyl (S)-4-[(S)-1-(Methoxycarbonyloxy)hexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-7)
|
505 |
8 |
0 |
|a 3.1.5 tert-Butyl (S)-4-[(R)-1-(Methoxycarbonyloxy)hexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-7)3.1.6 (2S,3S)-2-Benzamido-1-hydroxyoctadec-4-yn-3-yl Methyl Carbonate (syn-8); 3.1.7 (2S,3R)-2-Benzamido-1-hydroxyoctadec-4-yn-3-yl Methyl Carbonate (anti-8); 3.1.8 tert-Butyl (S)-4-[(R)-1-Chlorohexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-9); 3.1.9 tert-Butyl (S)-4-[(S)-1-Chlorohexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-9); 3.1.10 N-[(2S,3R)-3-Chloro-1-hydroxyoctadec-4-yn-2-yl]benzamide (syn-12)
|
505 |
8 |
0 |
|a 3.1.11 N-[(2S,3S)-3-Chloro-1-hydroxyoctadec-4-yn-2-yl]benzamide (anti-12)
|
520 |
|
|
|a The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26 per cent overall yield in seven steps), lysergic acid (4.0 per cent overall yield in fifteen steps), lysergol (3.6 per cent overall yield in fifteen steps) and isolysergol (8.2 per cent overall yield in eleven steps) have been achieved. These are
|
520 |
|
|
|a The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26 per cent overall yield in seven steps), lysergic acid (4.0 per cent overall yield in fifteen steps), lysergol (3.6 per cent overall yield in fifteen steps) and isolysergol (8.2 per cent overall yield in eleven steps) have been achieved. These are
|
650 |
|
0 |
|a Bioorganic chemistry
|
650 |
|
0 |
|a Catalysis
|
650 |
|
0 |
|a Chemistry
|
650 |
|
0 |
|a Chemistry
|
650 |
|
0 |
|a Bioorganic chemistry
|
650 |
|
0 |
|a Catalysis
|
776 |
1 |
|
|z 9784431540427
|
776 |
0 |
8 |
|i Buchausg. u.d.T.
|z 978-4-431-54042-7
|
856 |
4 |
0 |
|u https://doi.org/10.1007/978-4-431-54043-4
|x Verlag
|3 Volltext
|
856 |
4 |
0 |
|u http://dx.doi.org/10.1007/978-4-431-54043-4
|x Resolving-System
|z lizenzpflichtig
|3 Volltext
|
856 |
4 |
2 |
|u https://swbplus.bsz-bw.de/bsz355115832cov.jpg
|m V:DE-576
|m X:springer
|q image/jpeg
|v 20150513103910
|3 Cover
|
889 |
|
|
|w (DE-627)67592670X
|
912 |
|
|
|a ZDB-2-CMS
|
912 |
|
|
|a ZDB-2-CMS
|b 2012
|
935 |
|
|
|h GBV
|i ExPruef
|
951 |
|
|
|a BO
|
856 |
4 |
0 |
|u http://dx.doi.org/10.1007/978-4-431-54043-4
|9 DE-Ch1
|
852 |
|
|
|a DE-Ch1
|x epn:3342282819
|z 2011-12-16T14:45:47Z
|
972 |
|
|
|k Campuslizenz
|
972 |
|
|
|c EBOOK
|
852 |
|
|
|a DE-105
|x epn:3342282835
|z 2018-03-13T10:54:12Z
|
976 |
|
|
|h Elektronischer Volltext - Campuslizenz
|
856 |
4 |
0 |
|u http://dx.doi.org/10.1007/978-4-431-54043-4
|z Zum Online-Dokument
|9 DE-Zi4
|
852 |
|
|
|a DE-Zi4
|x epn:3342282851
|z 2012-11-10T04:11:46Z
|
856 |
4 |
0 |
|u http://dx.doi.org/10.1007/978-4-431-54043-4
|9 DE-520
|
852 |
|
|
|a DE-520
|x epn:3342282878
|z 2011-12-16T14:45:47Z
|
980 |
|
|
|a 1651097984
|b 0
|k 1651097984
|o 355115832
|
SOLR
_version_ |
1796700293404033024 |
author |
Inuki, Shinsuke |
author_facet |
Inuki, Shinsuke |
author_role |
aut |
author_sort |
Inuki, Shinsuke |
author_variant |
s i si |
callnumber-first |
Q - Science |
callnumber-label |
QD241-441 |
callnumber-raw |
QD241-441, QD181.S1 .I889 2012 |
callnumber-search |
QD241-441, QD181.S1 .I889 2012 |
callnumber-sort |
QD 3241 3441 |
callnumber-subject |
QD - Chemistry |
collection |
ZDB-2-CMS |
contents |
Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds; Supervisors' Foreword; Acknowledgments; Contents; 1 Introduction; Abstract; References; Part ITotal Synthesis of Pachastrissamine (Jaspine B); 2 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Bromoallenes; Abstract; 2.1…Experimental Section; 2.1.1 General Methods; 2.1.2 tert-Butyl (R)-4-[(R)-3-Bromopropa-1,2-dienyl]-2, 2-dimethyloxazolidine-3-carboxylate (12a); 2.1.3 N-[(2R,4R)-5-Bromo-1-hydroxypenta-3,4-dien-2-yl] benzamide (9a), 2.1.4 (3aS,6aS)-6-Methylene-2-phenyl-3a,4,6,6a -tetrahydrofuro[3,4-d]oxazole (8)2.1.5 (R)-N-[5-(Methoxymethyl)-2,3-dihydrofuran-3-yl] benzamide (13a); 2.1.6 (R)-N-{5-[(2,2,2-Trifluoroethoxy)methyl] -2,3-dihydrofuran-3-yl}benzamide (13b); 2.1.7 N-(5-Methylfuran-3-yl)benzamide (14); 2.1.8 tert-Butyl (R)-4-[(S)-3-Bromopropa-1,2-dienyl]-2, 2-dimethyloxazolidine-3-carboxylate (12b); 2.1.9 N-[(2R,4S)-5-Bromo-1-hydroxypenta -3,4-dien-2-yl]benzamide (9b); 2.1.10 [(3aS,6S,6aS)-2-Phenyl-3a,4,6,6a-tetrahydrofuro [3,4-d]oxazol-6-yl]methanol (15), 2.1.11 (3aS,6S,6aS)-2-Phenyl-6-tetradecyl-3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (16)2.1.12 (3aS,6S,6aS)-2-Phenyl-6-(3-phenylpropyl) -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17a); 2.1.13 (3aS,6S,6aS)-6-Ethyl-2-phenyl-3a,4,6, 6a-tetrahydrofuro[3,4-d]oxazole (17b); 2.1.14 (3aS,6S,6aS)-6-Isobutyl-2-phenyl-3a,4,6, 6a-tetrahydrofuro[3,4-d]oxazole (17c); 2.1.15 (3aS,6S,6aS)-6-(2-Methylallyl)-2-phenyl -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17d); 2.1.16 (1S,4S,7S)-5-(4-Phenylhepta-1,6-dien-4-yl) -2-oxa-5-azabicyclo[2.2.1]heptan-7-ol (18), 2.1.17 (3aS,6S,6aS)-6-(But-3-enyl)-2-phenyl -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17e)References; 3 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Propargyl Chlorides and Carbonates; Abstract; 3.1…Experimental Section; 3.1.1 General Methods; 3.1.2 tert-Butyl (S)-4-[(S)-1-Hydroxyhexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-6); 3.1.3 tert-Butyl (S)-4-[(R)-1-Hydroxyhexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-6); 3.1.4 tert-Butyl (S)-4-[(S)-1-(Methoxycarbonyloxy)hexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-7), 3.1.5 tert-Butyl (S)-4-[(R)-1-(Methoxycarbonyloxy)hexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-7)3.1.6 (2S,3S)-2-Benzamido-1-hydroxyoctadec-4-yn-3-yl Methyl Carbonate (syn-8); 3.1.7 (2S,3R)-2-Benzamido-1-hydroxyoctadec-4-yn-3-yl Methyl Carbonate (anti-8); 3.1.8 tert-Butyl (S)-4-[(R)-1-Chlorohexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-9); 3.1.9 tert-Butyl (S)-4-[(S)-1-Chlorohexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-9); 3.1.10 N-[(2S,3R)-3-Chloro-1-hydroxyoctadec-4-yn-2-yl]benzamide (syn-12), 3.1.11 N-[(2S,3S)-3-Chloro-1-hydroxyoctadec-4-yn-2-yl]benzamide (anti-12), The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26 per cent overall yield in seven steps), lysergic acid (4.0 per cent overall yield in fifteen steps), lysergol (3.6 per cent overall yield in fifteen steps) and isolysergol (8.2 per cent overall yield in eleven steps) have been achieved. These are |
ctrlnum |
(DE-627)1651097984, (DE-576)355115832, (DE-599)BSZ355115832, (OCoLC)838808974, (OCoLC)772669817, (DE-He213)978-4-431-54043-4 |
de105_date |
2018-03-13T10:54:12Z |
dech1_date |
2011-12-16T14:45:47Z |
dewey-full |
547, 546.723 |
dewey-hundreds |
500 - Natural sciences and mathematics |
dewey-ones |
547 - Organic chemistry, 546 - Inorganic chemistry |
dewey-raw |
547, 546.723 |
dewey-search |
547, 546.723 |
dewey-sort |
3547 |
dewey-tens |
540 - Chemistry and allied sciences |
doi_str_mv |
10.1007/978-4-431-54043-4 |
facet_912a |
ZDB-2-CMS |
facet_avail |
Online |
finc_class_facet |
Chemie und Pharmazie |
finc_id_str |
0003582188 |
fincclass_txtF_mv |
science-chemistry |
footnote |
Description based upon print version of record |
format |
eBook |
format_access_txtF_mv |
Book, E-Book |
format_de105 |
Ebook |
format_de14 |
Book, E-Book |
format_de15 |
Book, E-Book |
format_del152 |
Buch |
format_detail_txtF_mv |
text-online-monograph-independent |
format_dezi4 |
e-Book |
format_finc |
Book, E-Book |
format_legacy |
ElectronicBook |
format_legacy_nrw |
Book, E-Book |
format_nrw |
Book, E-Book |
format_strict_txtF_mv |
E-Book |
geogr_code |
not assigned |
geogr_code_person |
not assigned |
id |
0-1651097984 |
illustrated |
Not Illustrated |
imprint |
Tokyo, Springer Tokyo, 2012 |
imprint_str_mv |
Tokyo: Springer Tokyo, 2012 |
institution |
DE-105, DE-Zi4, DE-Ch1, DE-520 |
is_hierarchy_id |
|
is_hierarchy_title |
|
isbn |
9784431540434 |
isbn_isn_mv |
9784431540427, 978-4-431-54042-7 |
kxp_id_str |
1651097984 |
language |
English |
last_indexed |
2024-04-18T19:02:03.266Z |
local_heading_facet_dezwi2 |
Bioorganic chemistry, Catalysis, Chemistry |
marc024a_ct_mv |
10.1007/978-4-431-54043-4 |
marc_error |
[geogr_code]Unable to make public java.lang.AbstractStringBuilder java.lang.AbstractStringBuilder.append(java.lang.String) accessible: module java.base does not "opens java.lang" to unnamed module @d9403fb |
match_str |
inuki2012totalsynthesisofbioactivenaturalproductsbypalladiumcatalyzeddominocyclizationofallenesandrelatedcompounds |
mega_collection |
Verbunddaten SWB |
misc_de105 |
EBOOK |
oclc_num |
838808974, 772669817 |
physical |
Online-Ressource (XVI, 106p. 66 illus, digital) |
publishDate |
2012 |
publishDateSort |
2012 |
publishPlace |
Tokyo |
publisher |
Springer Tokyo |
record_format |
marcfinc |
record_id |
355115832 |
recordtype |
marcfinc |
rvk_facet |
No subject assigned |
series2 |
Springer Theses, SpringerLink ; Bücher |
source_id |
0 |
spelling |
Inuki, Shinsuke aut, Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds by Shinsuke Inuki, Tokyo Springer Tokyo 2012, Online-Ressource (XVI, 106p. 66 illus, digital), Text txt rdacontent, Computermedien c rdamedia, Online-Ressource cr rdacarrier, Springer Theses, SpringerLink Bücher, Description based upon print version of record, Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds; Supervisors' Foreword; Acknowledgments; Contents; 1 Introduction; Abstract; References; Part ITotal Synthesis of Pachastrissamine (Jaspine B); 2 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Bromoallenes; Abstract; 2.1…Experimental Section; 2.1.1 General Methods; 2.1.2 tert-Butyl (R)-4-[(R)-3-Bromopropa-1,2-dienyl]-2, 2-dimethyloxazolidine-3-carboxylate (12a); 2.1.3 N-[(2R,4R)-5-Bromo-1-hydroxypenta-3,4-dien-2-yl] benzamide (9a), 2.1.4 (3aS,6aS)-6-Methylene-2-phenyl-3a,4,6,6a -tetrahydrofuro[3,4-d]oxazole (8)2.1.5 (R)-N-[5-(Methoxymethyl)-2,3-dihydrofuran-3-yl] benzamide (13a); 2.1.6 (R)-N-{5-[(2,2,2-Trifluoroethoxy)methyl] -2,3-dihydrofuran-3-yl}benzamide (13b); 2.1.7 N-(5-Methylfuran-3-yl)benzamide (14); 2.1.8 tert-Butyl (R)-4-[(S)-3-Bromopropa-1,2-dienyl]-2, 2-dimethyloxazolidine-3-carboxylate (12b); 2.1.9 N-[(2R,4S)-5-Bromo-1-hydroxypenta -3,4-dien-2-yl]benzamide (9b); 2.1.10 [(3aS,6S,6aS)-2-Phenyl-3a,4,6,6a-tetrahydrofuro [3,4-d]oxazol-6-yl]methanol (15), 2.1.11 (3aS,6S,6aS)-2-Phenyl-6-tetradecyl-3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (16)2.1.12 (3aS,6S,6aS)-2-Phenyl-6-(3-phenylpropyl) -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17a); 2.1.13 (3aS,6S,6aS)-6-Ethyl-2-phenyl-3a,4,6, 6a-tetrahydrofuro[3,4-d]oxazole (17b); 2.1.14 (3aS,6S,6aS)-6-Isobutyl-2-phenyl-3a,4,6, 6a-tetrahydrofuro[3,4-d]oxazole (17c); 2.1.15 (3aS,6S,6aS)-6-(2-Methylallyl)-2-phenyl -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17d); 2.1.16 (1S,4S,7S)-5-(4-Phenylhepta-1,6-dien-4-yl) -2-oxa-5-azabicyclo[2.2.1]heptan-7-ol (18), 2.1.17 (3aS,6S,6aS)-6-(But-3-enyl)-2-phenyl -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17e)References; 3 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Propargyl Chlorides and Carbonates; Abstract; 3.1…Experimental Section; 3.1.1 General Methods; 3.1.2 tert-Butyl (S)-4-[(S)-1-Hydroxyhexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-6); 3.1.3 tert-Butyl (S)-4-[(R)-1-Hydroxyhexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-6); 3.1.4 tert-Butyl (S)-4-[(S)-1-(Methoxycarbonyloxy)hexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-7), 3.1.5 tert-Butyl (S)-4-[(R)-1-(Methoxycarbonyloxy)hexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-7)3.1.6 (2S,3S)-2-Benzamido-1-hydroxyoctadec-4-yn-3-yl Methyl Carbonate (syn-8); 3.1.7 (2S,3R)-2-Benzamido-1-hydroxyoctadec-4-yn-3-yl Methyl Carbonate (anti-8); 3.1.8 tert-Butyl (S)-4-[(R)-1-Chlorohexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-9); 3.1.9 tert-Butyl (S)-4-[(S)-1-Chlorohexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-9); 3.1.10 N-[(2S,3R)-3-Chloro-1-hydroxyoctadec-4-yn-2-yl]benzamide (syn-12), 3.1.11 N-[(2S,3S)-3-Chloro-1-hydroxyoctadec-4-yn-2-yl]benzamide (anti-12), The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26 per cent overall yield in seven steps), lysergic acid (4.0 per cent overall yield in fifteen steps), lysergol (3.6 per cent overall yield in fifteen steps) and isolysergol (8.2 per cent overall yield in eleven steps) have been achieved. These are, Bioorganic chemistry, Catalysis, Chemistry, 9784431540427, Buchausg. u.d.T. 978-4-431-54042-7, https://doi.org/10.1007/978-4-431-54043-4 Verlag Volltext, http://dx.doi.org/10.1007/978-4-431-54043-4 Resolving-System lizenzpflichtig Volltext, https://swbplus.bsz-bw.de/bsz355115832cov.jpg V:DE-576 X:springer image/jpeg 20150513103910 Cover, (DE-627)67592670X, http://dx.doi.org/10.1007/978-4-431-54043-4 DE-Ch1, DE-Ch1 epn:3342282819 2011-12-16T14:45:47Z, DE-105 epn:3342282835 2018-03-13T10:54:12Z, http://dx.doi.org/10.1007/978-4-431-54043-4 Zum Online-Dokument DE-Zi4, DE-Zi4 epn:3342282851 2012-11-10T04:11:46Z, http://dx.doi.org/10.1007/978-4-431-54043-4 DE-520, DE-520 epn:3342282878 2011-12-16T14:45:47Z |
spellingShingle |
Inuki, Shinsuke, Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds, Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds; Supervisors' Foreword; Acknowledgments; Contents; 1 Introduction; Abstract; References; Part ITotal Synthesis of Pachastrissamine (Jaspine B); 2 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Bromoallenes; Abstract; 2.1…Experimental Section; 2.1.1 General Methods; 2.1.2 tert-Butyl (R)-4-[(R)-3-Bromopropa-1,2-dienyl]-2, 2-dimethyloxazolidine-3-carboxylate (12a); 2.1.3 N-[(2R,4R)-5-Bromo-1-hydroxypenta-3,4-dien-2-yl] benzamide (9a), 2.1.4 (3aS,6aS)-6-Methylene-2-phenyl-3a,4,6,6a -tetrahydrofuro[3,4-d]oxazole (8)2.1.5 (R)-N-[5-(Methoxymethyl)-2,3-dihydrofuran-3-yl] benzamide (13a); 2.1.6 (R)-N-{5-[(2,2,2-Trifluoroethoxy)methyl] -2,3-dihydrofuran-3-yl}benzamide (13b); 2.1.7 N-(5-Methylfuran-3-yl)benzamide (14); 2.1.8 tert-Butyl (R)-4-[(S)-3-Bromopropa-1,2-dienyl]-2, 2-dimethyloxazolidine-3-carboxylate (12b); 2.1.9 N-[(2R,4S)-5-Bromo-1-hydroxypenta -3,4-dien-2-yl]benzamide (9b); 2.1.10 [(3aS,6S,6aS)-2-Phenyl-3a,4,6,6a-tetrahydrofuro [3,4-d]oxazol-6-yl]methanol (15), 2.1.11 (3aS,6S,6aS)-2-Phenyl-6-tetradecyl-3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (16)2.1.12 (3aS,6S,6aS)-2-Phenyl-6-(3-phenylpropyl) -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17a); 2.1.13 (3aS,6S,6aS)-6-Ethyl-2-phenyl-3a,4,6, 6a-tetrahydrofuro[3,4-d]oxazole (17b); 2.1.14 (3aS,6S,6aS)-6-Isobutyl-2-phenyl-3a,4,6, 6a-tetrahydrofuro[3,4-d]oxazole (17c); 2.1.15 (3aS,6S,6aS)-6-(2-Methylallyl)-2-phenyl -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17d); 2.1.16 (1S,4S,7S)-5-(4-Phenylhepta-1,6-dien-4-yl) -2-oxa-5-azabicyclo[2.2.1]heptan-7-ol (18), 2.1.17 (3aS,6S,6aS)-6-(But-3-enyl)-2-phenyl -3a,4,6,6a-tetrahydrofuro[3,4-d]oxazole (17e)References; 3 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Propargyl Chlorides and Carbonates; Abstract; 3.1…Experimental Section; 3.1.1 General Methods; 3.1.2 tert-Butyl (S)-4-[(S)-1-Hydroxyhexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-6); 3.1.3 tert-Butyl (S)-4-[(R)-1-Hydroxyhexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-6); 3.1.4 tert-Butyl (S)-4-[(S)-1-(Methoxycarbonyloxy)hexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-7), 3.1.5 tert-Butyl (S)-4-[(R)-1-(Methoxycarbonyloxy)hexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-7)3.1.6 (2S,3S)-2-Benzamido-1-hydroxyoctadec-4-yn-3-yl Methyl Carbonate (syn-8); 3.1.7 (2S,3R)-2-Benzamido-1-hydroxyoctadec-4-yn-3-yl Methyl Carbonate (anti-8); 3.1.8 tert-Butyl (S)-4-[(R)-1-Chlorohexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (syn-9); 3.1.9 tert-Butyl (S)-4-[(S)-1-Chlorohexadec-2-yn-1-yl]-2,2-dimethyloxazolidine-3-carboxylate (anti-9); 3.1.10 N-[(2S,3R)-3-Chloro-1-hydroxyoctadec-4-yn-2-yl]benzamide (syn-12), 3.1.11 N-[(2S,3S)-3-Chloro-1-hydroxyoctadec-4-yn-2-yl]benzamide (anti-12), The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26 per cent overall yield in seven steps), lysergic acid (4.0 per cent overall yield in fifteen steps), lysergol (3.6 per cent overall yield in fifteen steps) and isolysergol (8.2 per cent overall yield in eleven steps) have been achieved. These are, Bioorganic chemistry, Catalysis, Chemistry |
swb_id_str |
355115832 |
title |
Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds |
title_auth |
Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds |
title_full |
Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds by Shinsuke Inuki |
title_fullStr |
Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds by Shinsuke Inuki |
title_full_unstemmed |
Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds by Shinsuke Inuki |
title_short |
Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds |
title_sort |
total synthesis of bioactive natural products by palladium-catalyzed domino cyclization of allenes and related compounds |
title_unstemmed |
Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds |
topic |
Bioorganic chemistry, Catalysis, Chemistry |
topic_facet |
Bioorganic chemistry, Catalysis, Chemistry |
url |
https://doi.org/10.1007/978-4-431-54043-4, http://dx.doi.org/10.1007/978-4-431-54043-4, https://swbplus.bsz-bw.de/bsz355115832cov.jpg |
work_keys_str_mv |
AT inukishinsuke totalsynthesisofbioactivenaturalproductsbypalladiumcatalyzeddominocyclizationofallenesandrelatedcompounds |