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Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction...
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| Zeitschriftentitel: | Liebigs Annalen der Chemie |
|---|---|
| Personen und Körperschaften: | , , |
| In: | Liebigs Annalen der Chemie, 1990, 1990, 3, S. 253-260 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Tietze, Lutz F. Meier, Heinrich Nutt, Heinrich Tietze, Lutz F. Meier, Heinrich Nutt, Heinrich |
|---|---|
| author |
Tietze, Lutz F. Meier, Heinrich Nutt, Heinrich |
| spellingShingle |
Tietze, Lutz F. Meier, Heinrich Nutt, Heinrich Liebigs Annalen der Chemie Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction Organic Chemistry Physical and Theoretical Chemistry |
| author_sort |
tietze, lutz f. |
| spelling |
Tietze, Lutz F. Meier, Heinrich Nutt, Heinrich 0170-2041 Wiley Organic Chemistry Physical and Theoretical Chemistry http://dx.doi.org/10.1002/jlac.199019900146 <jats:title>Abstract</jats:title><jats:p>The tandem Knoevenagel hetero Diels‐Alder reaction of 4,4,4‐trichloro‐3‐oxobutanal (<jats:bold>4</jats:bold>), the malondialdehyde derivative <jats:bold>11a</jats:bold>, and the enol ether <jats:bold>13</jats:bold> was followed by separation of the diastereomers and treatment with DBU in methanol. Thermolysis in xylene then gave the secologanin derivative <jats:bold>25a</jats:bold> in 14% yield with the correct relative stereochemistry at all stereogenic centers. Hydrolysis of the dithiane moiety afforded secologanin aglucone <jats:italic>O</jats:italic>‐ethyl ether <jats:bold>9</jats:bold> in 86% yield. In a similar way, <jats:bold>25b</jats:bold> and <jats:bold>25c</jats:bold> were obtained in 14% and 28% yield from the malondialdehyde derivatives <jats:bold>11b</jats:bold> and <jats:bold>11c</jats:bold>, respectively. Reduction of <jats:bold>9</jats:bold> with sodium borohydride gave swerosid aglucone <jats:italic>O</jats:italic>‐ethyl ether <jats:bold>24</jats:bold> in 69% yield. The dihydrosecologanin derivative <jats:bold>32</jats:bold> was obtained in 20% yield by reaction of <jats:bold>5, 11c</jats:bold>, and <jats:bold>26</jats:bold> followed by methanolysis. In this transformation the initially formed cycloadducts <jats:bold>27</jats:bold> and <jats:bold>28</jats:bold> were isolated; <jats:bold>33</jats:bold>, the other type of product obtained by reaction of the second heterodiene moiety in the intermediate Knoevenagel product <jats:bold>18</jats:bold>, was also found.</jats:p> Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone <i>O</i>‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction Liebigs Annalen der Chemie |
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tietze1990interandintramolecularheterodielsalderreactions28synthesisofsecologaninagluconeoethyletherandderivativesbytandemknoevenagelheterodielsalderreaction |
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Liebigs Annalen der Chemie |
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| title |
Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_unstemmed |
Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_full |
Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_fullStr |
Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_full_unstemmed |
Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_short |
Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_sort |
inter‐ and intramolecular hetero diels‐alder reactions, 28. synthesis of (±)‐secologanin aglucone <i>o</i>‐ethyl ether and derivatives by tandem knoevenagel hetero diels‐alder reaction |
| topic |
Organic Chemistry Physical and Theoretical Chemistry |
| url |
http://dx.doi.org/10.1002/jlac.199019900146 |
| publishDate |
1990 |
| physical |
253-260 |
| description |
<jats:title>Abstract</jats:title><jats:p>The tandem Knoevenagel hetero Diels‐Alder reaction of 4,4,4‐trichloro‐3‐oxobutanal (<jats:bold>4</jats:bold>), the malondialdehyde derivative <jats:bold>11a</jats:bold>, and the enol ether <jats:bold>13</jats:bold> was followed by separation of the diastereomers and treatment with DBU in methanol. Thermolysis in xylene then gave the secologanin derivative <jats:bold>25a</jats:bold> in 14% yield with the correct relative stereochemistry at all stereogenic centers. Hydrolysis of the dithiane moiety afforded secologanin aglucone <jats:italic>O</jats:italic>‐ethyl ether <jats:bold>9</jats:bold> in 86% yield. In a similar way, <jats:bold>25b</jats:bold> and <jats:bold>25c</jats:bold> were obtained in 14% and 28% yield from the malondialdehyde derivatives <jats:bold>11b</jats:bold> and <jats:bold>11c</jats:bold>, respectively. Reduction of <jats:bold>9</jats:bold> with sodium borohydride gave swerosid aglucone <jats:italic>O</jats:italic>‐ethyl ether <jats:bold>24</jats:bold> in 69% yield. The dihydrosecologanin derivative <jats:bold>32</jats:bold> was obtained in 20% yield by reaction of <jats:bold>5, 11c</jats:bold>, and <jats:bold>26</jats:bold> followed by methanolysis. In this transformation the initially formed cycloadducts <jats:bold>27</jats:bold> and <jats:bold>28</jats:bold> were isolated; <jats:bold>33</jats:bold>, the other type of product obtained by reaction of the second heterodiene moiety in the intermediate Knoevenagel product <jats:bold>18</jats:bold>, was also found.</jats:p> |
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| author | Tietze, Lutz F., Meier, Heinrich, Nutt, Heinrich |
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| description | <jats:title>Abstract</jats:title><jats:p>The tandem Knoevenagel hetero Diels‐Alder reaction of 4,4,4‐trichloro‐3‐oxobutanal (<jats:bold>4</jats:bold>), the malondialdehyde derivative <jats:bold>11a</jats:bold>, and the enol ether <jats:bold>13</jats:bold> was followed by separation of the diastereomers and treatment with DBU in methanol. Thermolysis in xylene then gave the secologanin derivative <jats:bold>25a</jats:bold> in 14% yield with the correct relative stereochemistry at all stereogenic centers. Hydrolysis of the dithiane moiety afforded secologanin aglucone <jats:italic>O</jats:italic>‐ethyl ether <jats:bold>9</jats:bold> in 86% yield. In a similar way, <jats:bold>25b</jats:bold> and <jats:bold>25c</jats:bold> were obtained in 14% and 28% yield from the malondialdehyde derivatives <jats:bold>11b</jats:bold> and <jats:bold>11c</jats:bold>, respectively. Reduction of <jats:bold>9</jats:bold> with sodium borohydride gave swerosid aglucone <jats:italic>O</jats:italic>‐ethyl ether <jats:bold>24</jats:bold> in 69% yield. The dihydrosecologanin derivative <jats:bold>32</jats:bold> was obtained in 20% yield by reaction of <jats:bold>5, 11c</jats:bold>, and <jats:bold>26</jats:bold> followed by methanolysis. In this transformation the initially formed cycloadducts <jats:bold>27</jats:bold> and <jats:bold>28</jats:bold> were isolated; <jats:bold>33</jats:bold>, the other type of product obtained by reaction of the second heterodiene moiety in the intermediate Knoevenagel product <jats:bold>18</jats:bold>, was also found.</jats:p> |
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| id | ai-49-aHR0cDovL2R4LmRvaS5vcmcvMTAuMTAwMi9qbGFjLjE5OTAxOTkwMDE0Ng |
| imprint | Wiley, 1990 |
| imprint_str_mv | Wiley, 1990 |
| institution | DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229 |
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| issn_str_mv | 0170-2041 |
| language | English |
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| match_str | tietze1990interandintramolecularheterodielsalderreactions28synthesisofsecologaninagluconeoethyletherandderivativesbytandemknoevenagelheterodielsalderreaction |
| mega_collection | Wiley (CrossRef) |
| physical | 253-260 |
| publishDate | 1990 |
| publishDateSort | 1990 |
| publisher | Wiley |
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| series | Liebigs Annalen der Chemie |
| source_id | 49 |
| spelling | Tietze, Lutz F. Meier, Heinrich Nutt, Heinrich 0170-2041 Wiley Organic Chemistry Physical and Theoretical Chemistry http://dx.doi.org/10.1002/jlac.199019900146 <jats:title>Abstract</jats:title><jats:p>The tandem Knoevenagel hetero Diels‐Alder reaction of 4,4,4‐trichloro‐3‐oxobutanal (<jats:bold>4</jats:bold>), the malondialdehyde derivative <jats:bold>11a</jats:bold>, and the enol ether <jats:bold>13</jats:bold> was followed by separation of the diastereomers and treatment with DBU in methanol. Thermolysis in xylene then gave the secologanin derivative <jats:bold>25a</jats:bold> in 14% yield with the correct relative stereochemistry at all stereogenic centers. Hydrolysis of the dithiane moiety afforded secologanin aglucone <jats:italic>O</jats:italic>‐ethyl ether <jats:bold>9</jats:bold> in 86% yield. In a similar way, <jats:bold>25b</jats:bold> and <jats:bold>25c</jats:bold> were obtained in 14% and 28% yield from the malondialdehyde derivatives <jats:bold>11b</jats:bold> and <jats:bold>11c</jats:bold>, respectively. Reduction of <jats:bold>9</jats:bold> with sodium borohydride gave swerosid aglucone <jats:italic>O</jats:italic>‐ethyl ether <jats:bold>24</jats:bold> in 69% yield. The dihydrosecologanin derivative <jats:bold>32</jats:bold> was obtained in 20% yield by reaction of <jats:bold>5, 11c</jats:bold>, and <jats:bold>26</jats:bold> followed by methanolysis. In this transformation the initially formed cycloadducts <jats:bold>27</jats:bold> and <jats:bold>28</jats:bold> were isolated; <jats:bold>33</jats:bold>, the other type of product obtained by reaction of the second heterodiene moiety in the intermediate Knoevenagel product <jats:bold>18</jats:bold>, was also found.</jats:p> Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone <i>O</i>‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction Liebigs Annalen der Chemie |
| spellingShingle | Tietze, Lutz F., Meier, Heinrich, Nutt, Heinrich, Liebigs Annalen der Chemie, Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction, Organic Chemistry, Physical and Theoretical Chemistry |
| title | Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_full | Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_fullStr | Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_full_unstemmed | Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_short | Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| title_sort | inter‐ and intramolecular hetero diels‐alder reactions, 28. synthesis of (±)‐secologanin aglucone <i>o</i>‐ethyl ether and derivatives by tandem knoevenagel hetero diels‐alder reaction |
| title_unstemmed | Inter‐ and intramolecular hetero Diels‐Alder reactions, 28. Synthesis of (±)‐secologanin aglucone O‐ethyl ether and derivatives by tandem Knoevenagel hetero Diels‐Alder reaction |
| topic | Organic Chemistry, Physical and Theoretical Chemistry |
| url | http://dx.doi.org/10.1002/jlac.199019900146 |