Synthesis of trans,trans,cis-fused tetracyclic skeleton via radical domino cyclization

被引：8

作者：

Furuta, Miyu ^{[1
]}

Hanaya, Kengo ^{[1
]}

Sugai, Takeshi ^{[1
]}

Shoji, Mitsuru ^{[1
]}

机构：

[1] Keio Univ, Dept Pharmaceut Sci, Fac Pharm, Minato Ku, I-5-30 Shibakoen, Tokyo 1058512, Japan

来源：

TETRAHEDRON | 2017年 / 73卷 / 16期

关键词：

Limonoid; Tetracyclic core; Domino cyclization; Radical cyclization; Stereoselective; LIMONOIDS;

D O I：

10.1016/j.tet.2017.03.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Limonoids are characterized by a polycyclic structure and show a wide variety of bioactivities. In particular, mesendanin L, 12-hydroxyamoorastatone, and meliatoosenin F have unique structures containing a trans-A/B/C and cis-C/D-fused tetracyclic skeleton. We synthesized the core structure of these limonoids via Mn(OAc)(3) and Cu(OAc)(2)-mediated radical domino cyclization of an acyclic tetraene precursor having a terminal beta-keto ester. To the best of our knowledge, this is the first example of the radical-mediated construction of a 6/6/6/5-membered tetracyclic skeleton. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2316 / 2322

页数：7

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