Construction of the ABCE-ring structure of talatisamine via decarboxylative radical cyclization

被引：11

作者：

Minagawa, Kosuke ^{[1
]}

Kamakura, Daiki ^{[1
]}

Hagiwara, Koichi ^{[1
]}

Inoue, Masayuki ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 2020年 / 76卷 / 35期

关键词：

Alkaloids; Cyclization; Radical reactions; Terpenoids; Total synthesis; STEREOSPECIFIC TOTAL-SYNTHESIS; CARBOXYLIC-ACIDS; VISIBLE-LIGHT; ALKALOIDS; MILD;

D O I：

10.1016/j.tet.2020.131385

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Talatisamine (1) is a C-19-diterpenoid alkaloid with a synthetically challenging hexacyclic ABCDEF-ring structure. Herein we report a radical-based strategy for constructing the 6/7/5/6-membered ABCE-ring 8a. After assembling the 3 known fragments, an AE-ring, an allylstannane, and a C-ring, irradiation of the ACE-ring with Hg lamp in the presence of phenanthrene and 1,4-dicyanobenzene promoted decarboxylative formation of the C11-bridgehead radical, which cyclized into the 7-membered B-ring with stereoselective installation of the C9,10-tertiary carbons of 8a. (C) 2020 Elsevier Ltd. All rights reserved.

引用

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