Total Synthesis of Cochlearol B via Intramolecular [2+2] Photocycloaddition

被引：19

作者：

Mashiko, Tomoya ^{[1
]}

Shingai, Yuta ^{[1
]}

Sakai, Jun ^{[1
]}

Kamo, Shogo ^{[1
]}

Adachi, Shinya ^{[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：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 46期

关键词：

cochlearol B; intramolecular [2+2] photocycloaddition; natural product; oxidative cyclization; total synthesis; CONSTRUCTION; EFFICIENT; GANODERMA; BONDS;

D O I：

10.1002/anie.202110556

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we describe the first total synthesis of cochlearol B, a meroterpenoid natural product featuring a 4/5/6/6/6-fused pentacyclic structure. Key steps, oxidative cyclization and subsequent intramolecular [2+2] photocycloaddition, which constructed the pentacyclic structure in highly stereoselective manner, allowed efficient access to cochlearol B with the longest linear sequence of 16 steps, and in 9 % overall yield. Single-crystal X-ray crystallographic analysis clearly confirmed the stereochemistry of cochlearol B.

引用

页码：24484 / 24487

页数：4

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