A concise synthesis of marine natural product (-)-15-oxopuupehenol from (+)-sclarelide

被引：3

作者：

Cheng, Yun-Fei ^{[1
]}

Li, Hui-Jing ^{[1
,2
]}

Zhang, Yin-Lin ^{[1
]}

Wu, Yan-Chao ^{[1
]}

机构：

[1] Harbin Inst Technol, Weihai Marine Organism & Med Technol Res Inst, Weihai, Peoples R China

[2] Weihai Huiankang Biotechnol Co Ltd, Weihai, Peoples R China

来源：

NATURAL PRODUCT RESEARCH | 2023年 / 37卷 / 08期

基金：

中国国家自然科学基金;

关键词：

Marine natural product; step-economical synthesis; (-)-15-oxopuupehenol; (+)-sclarelide; ENANTIOSPECIFIC SYNTHESIS; PUUPEHENONE; METABOLITES;

D O I：

10.1080/14786419.2021.2000983

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A step-economical synthesis of (-)-15-oxopuupehenol from cheap and readily available (+)-sclarelide is achieved with 20.3% overall yield in 9 steps. The key features of this synthetic mythology include a palladium catalyzed tandem carbine migratory insertion reaction to construct the key skeleton, a DDQ-mediated isomerization/oxidation of allyl alcohol to afford alpha, beta-unsaturated ketone, and a NaOH-induced intramolecular Michael addition followed by acetonide deprotection to give (-)-15-oxopuupehenol.

引用

页码：1265 / 1270

页数：6

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