Enantioselective total synthesis of 3-epi-ottelione A

被引：11

作者：

Araki, H

Inoue, M

Katoh, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Elect Chem, Yokohama, Kanagawa 2268502, Japan

[2] Sagami Chem Res Ctr, Kanagawa 2521193, Japan

来源：

SYNLETT | 2003年 / 15期

关键词：

3-epi-ottelione A; total synthesis; otteliones A and B; natural products; antitumor agents;

D O I：

10.1055/s-2003-42114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective total synthesis of (+)-3-epi-ottelione A (2), the earlier proposed stereostructure of the antitumor natural product ottelione A (4), was achieved for the first time starting from the known tetracyclic compound 9. The synthesis involves the following three crucial steps: (i) a coupling reaction of aldehyde 8 and aryllithium 7 to introduce the aromatic portion, (ii) base-induced lactol-opening/epimerization at the C1 position of 6 to deliver the requisite hydrindane 15, and (iii) Corey-Winter's reductive olefination of the cyclic thiocarbonate 19 to install the C5-C6 double bond.

引用

页码：2401 / 2403

页数：3

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