Asymmetric Formal Synthesis of Azadirachtin

被引：17

作者：

Mori, Naoki ^{[1
]}

Kitahara, Takeshi

Mori, Kenji

Watanabe, Hidenori ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 49期

关键词：

acetals; cyclizations; natural products; radicals; stereoselectivity; CROWDED C8-C-14 BOND; RELAY ROUTE; PART; CONSTRUCTION; NMR; CHEMISTRY; INDICA; ENTRY; MODEL;

D O I：

10.1002/anie.201507935

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric formal synthesis of azadirachtin, a potent insect antifeedant, was accomplished in 30 steps to Ley's synthetic intermediate (longest linear sequence). The synthesis features: 1) rapid access to the optically active right-hand segment starting from the known 5-hydroxymethyl-2-cyclopentenone scaffold; 2) construction of the B and E rings by a key intramolecular tandem radical cyclization; 3) formation of the hemiacetal moiety in the C ring through the alpha-oxidation of the six-membered lactone followed by methanolysis.

引用

页码：14920 / 14923

页数：4

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