Total Synthesis of Leucosceptroids A and B

被引：36

作者：

Guo, Sheng ^{[1
]}

Liu, Jie ^{[1
]}

Ma, Dawei ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 04期

基金：

中国国家自然科学基金;

关键词：

aldol reaction; cyclization; natural products; sesterterpenoids; total synthesis; DEFENSIVE SESTERTERPENOIDS; GLANDULAR TRICHOMES; CANUM; CYCLIZATION; HYDROSILYLATION; TERPENOIDS; INDUCTION; ALCOHOLS; KETONES; ACCESS;

D O I：

10.1002/anie.201410134

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

LeucosceptroidsA and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram-scale total synthesis of leucosceptroidB and the first total synthesis of leucosceptroidA are presented. The key transformations include an aldol reaction between a substituted dihydrofuranone and an (S)-citronellal-derived aldehyde, a SmI2-mediated intramolecular ketyl-olefin radical cyclization, and final-stage alcohol oxidation.

引用

页码：1298 / 1301

页数：4

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