41 Total Synthesis of 13-Oxyingenols(Oral Presentation)
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- Ohyoshi Takayuki
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Funakubo Shota
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Miyazawa Yamato
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Niida Keisuke
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Asuma Yuki
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Aoki Kenta
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Ohmura Satomi
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Hayakawa Ichiro
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Kigoshi Hideo
- Graduate School of Pure and Applied Sciences, University of Tsukuba
Bibliographic Information
- Other Title
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- 41 13-オキシインゲノール類の全合成(口頭発表の部)
Abstract
13-Oxyingenol derivative 1 and ingenol (3) are diterpenoids isolated from the plants of Euphorbia sp. The main structural features of ingenols are a bicyclo[4.4.1]undecane skeleton with inside-outside intrabridgehead stereochemistry and a high degree of oxygenation. They and their analogues showed interesting bioactivities. The molecular complexity of ingenol derivatives, in conjunction with their potent bioactivities, has made them attractive synthetic targets. We have achieved the first total synthesis of (-)-13-oxyingenol (2) and its natural derivative 1. The efficient functionalization of the A- and B-ring parts was established by using C-2 and C-7 hydroxy groups as clues. This approach is highlighted by RCM for the construction of an inside-outside framework, regio- and stereoselective dihydroxylation for the functionalization of the A-ring, and [2,3]-sigmalropic rearrangement for the functionalization of the B-ring.
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 54 (0), 241-246, 2012
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
- 1390282681056354176
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- NII Article ID
- 110010013834
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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