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.
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页码：2316 / 2322
页数：7
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