Novel Radical Cyclization Cascade for the Unified Synthesis of the Cedrane and Clovane Sesquiterpene Skeletons

被引：0

作者：

Suzuki, Takahiro ^{[1
]}

Yamashita, Kotaro ^{[2
]}

Ikeda, Wataru ^{[2
]}

Ikeuchi, Kazutada ^{[1
,3
]}

Tanino, Keiji ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

[2] Hokkaido Univ, Grad Sch Chem Sci & Engn, Sapporo, Hokkaido 0600810, Japan

[3] Nagoya City Univ, Grad Sch Pharmaceut Sci, 3-1 Tanabe Dori,Mizuho Ku, Nagoya 4678603, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 13卷 / 09期

关键词：

Cyclization; Cascade reactions; Epoxides; Radical reactions; Sesquiterpenes; ASYMMETRIC TOTAL-SYNTHESIS; MICROBIAL TRANSFORMATION; 3+2+1 CYCLOADDITION; CEDRENE; DITERPENOIDS; TERPENOIDS; CONSTRUCTION; CP2TICL; CEDROL;

D O I：

10.1002/ajoc.202400242

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical cyclization cascade reactions of epoxycyclohexanes possessing alkene and alkyne side chains have been achieved. Sequential 5- or 6-exo-trig/5-exo-dig reactions triggered by epoxide ring opening with Cp2TiCl were found to provide a useful unified synthetic method for generating the carbon skeletons of clovane and cedrane, two tricyclic sesquiterpenes. The factors responsible for the development of stereoselectivity during cyclization are also discussed. Radical cyclization cascade reactions of epoxycyclohexanes possessing alkene and alkyne side chains have been achieved. Sequential 5- or 6-exo-trig/5-exo-dig reactions triggered by epoxide ring opening with Cp2TiCl were found to provide a useful unified synthetic method for generating the tricyclic carbon skeletons of clovane and cedrane, which are used as fragrance ingredients and show various biological activities. image

引用

页数：5

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