73 STUDIES ON A NEW SYNTHESIS OF THE ACYCLIC AMIDE AND MACROCYCLIC LACTAM ALKALOIDS
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- Nagao Y.
- Institute for Chemical Research, Kyoto University
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- Seno K.
- Institute for Chemical Research, Kyoto University
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- Miyasaka T.
- Institute for Chemical Research, Kyoto University
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- Kawabata K.
- Institute for Chemical Research, Kyoto University
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- Takao S.
- Institute for Chemical Research, Kyoto University
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- Fujita E.
- Institute for Chemical Research, Kyoto University
Bibliographic Information
- Other Title
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- 73 非環状アミドアルカロイドならびに大環状ラクタムアルカロイドの新合成研究
Abstract
An efficiently monitored aminolysis of 3-acylthiazolidine-2-thione (1) has been found to give a very high yield of amide (6). Experimental results are shown in Table 2. The similar aminolysis of 3-hexadecanoylthiazolidine-2-thione (1c) with many kinds of aminoalcohols resulted in the chemospecific formation of the desired hydroxyamides in satisfactory yields. (See Table 3.) Subsequently, naturally occurring amide alkaloids, fagaramide (14), dolichotheline (16), and maytenine (18) were synthesized in good yields by the application of the foregoing aminolysis. Synthesis of macrocyclic lactams was also successfully carried out. (See Table 4.) The total synthesis of codonocarpine (37), a macrocyclic spermidine alkaloid,utilizing this aminolysis as a key step is now in progress.
Journal
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- Symposium on the Chemistry of Natural Products, symposium papers
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Symposium on the Chemistry of Natural Products, symposium papers 22 (0), 554-561, 1979
Symposium on the Chemistry of Natural Products Steering Committee
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Details 詳細情報について
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- CRID
- 1390282681049381760
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- NII Article ID
- 110006678100
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- ISSN
- 24331856
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- Text Lang
- ja
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed