Total syntheses of (±)-penicibilaenes A and B via intramolecular aldol condensation

被引：6

作者：

Matsuo, Rintaro ^{[1
]}

Watanabe, Ayumu ^{[1
]}

Kamo, Shogo ^{[1
]}

Matsuzawa, Akinobu ^{[1
]}

Sugita, Kazuyuki ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Dept Synthet Med Chem, Shinagawa Ku, 2-4-41 Ebara, Tokyo 1428501, Japan

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 21期

关键词：

CONJUGATE ADDITION; ALCOHOLS;

D O I：

10.1039/d1qo01251g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, concise total syntheses of Peniclillium sesquiterpenes (+/-)-Penicibilaenes A and B are described. This approach involves an effective intramolecular aldol condensation to construct a bicyclic skeleton, a stereoselective rhodium-catalyzed 1,4-addition, a ring-closing metathesis, and several effective transformations that lead to (+/-)-penicibilaenes A and B with longest linear sequences of 12 and 13 steps, respectively. These transformations utilize commercial materials and are achieved in 4.0% overall yields for both compounds.

引用

页码：6063 / 6066

页数：4

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