Norrisolide: Total synthesis and related studies

被引：50
作者：
Brady, TP [1 ]
Kim, SH [1 ]
Wen, K [1 ]
Kim, C [1 ]
Theodorakis, EA [1 ]
机构：
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2005年 / 11卷 / 24期
关键词：
natural products; oxidation; synthetic methods; terpenoids; total synthesis;
D O I：
10.1002/chem.200500513
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A stereoselective synthesis of (+)-norrisolide is presented. This natural product belongs to a family of marine spongiane diterpenes the structure of which is characterized by a fused gamma-lactone-gamma-lactol ring system attached to a bicyclic hydrophobic core. Our studies led to the development of a expedient synthesis of such gamma-lactone-gamma-lactol motifs based on ring expansion of a fused cyclopropyl ester. Highlights of the synthetic strategy toward norrisolide include the coupling of the two bicyclic systems by constructing a sterically demanding C9-C10 bond and the installation of the C19 oxygen at the last step of the synthesis via a Baeyer-Villiger oxidation.
引用
收藏
页码：7175 / 7190
页数：16
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