New synthetic methodfor efficient synthesis of bioactive natural products -biomimetic synthesis of chaxines

被引：0
作者：
Nishikawa T. [1 ]
机构：
[1] Graduate Scnool of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya
来源：
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry | 2020年 / 78卷 / 06期
关键词：
Baeyer-Villiger oxidation; Biosynthesis; Chaxine; Electrocyclic reaction; Natural product; Oxidative cascade;
D O I：
10.5059/yukigoseikyokaishi.78.566
中图分类号：
学科分类号：
摘要：
Chaxine and its analogues, isolated from a Chinese edible mushroom, are highly oxidized steroidal natural products. This paper describes our proposed biosynthetic routes of chaxines and an eight-step synthesis of chaxines from ergosterol, on the basis of our biosynthetic proposal, which includes photo-induced 6-7r-electrocyclic reaction of ergosterol, site and regioselective Baeyer-Villiger oxidation of 2-ene-1,4-dione, and acyloxy migration of epoxide of the resulting enol ester as key steps. This biomimetic synthesis enabled us to revise the structures of chaxine B and its analogues proposed by the spectroscopic analysis. © 2020 Society of Synthetic Organic Chemistry. All rights reserved.
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页码：566 / 574
页数：8
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