First total synthesis of (±)-methyl gummiferolate using a homoallyl-homoallyl radical rearrangement reaction

被引：22

作者：

Toyota, M ^{[1
]}

Yokota, M ^{[1
]}

Ihara, M ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 10期

关键词：

D O I：

10.1021/ol990264u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of (+/-)-methyl gummiferolate (Ib) has been achieved with a high diastereoselectivity. The key steps included the homoallyl-homoallyl radical rearrangement reaction of the enyne 8 to afford the suitably functionalized bicyclo[2.2.2]octane 9 and the intramolecular Diels-Alder reaction of the tetraene 12 for the construction of the AB ring system of Ib.

引用

页码：1627 / 1629

页数：3

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