Stereoselective construction of quaternary chiral centers using Ti(III)-mediated opening of 2,3-epoxy alcohols: studies directed toward the synthesis of penifulvins

被引：17
|
作者：
Chakraborty, Tushar Kanti [1 ]
Chattopadhyay, Amit Kumar [2 ]
Samanta, Rajarshi [2 ]
Ampapathi, Ravi Sankar [1 ]
机构：
[1] CSIR, Cent Drug Res Inst, Lucknow 226001, Uttar Pradesh, India
[2] CSIR, Indian Inst Chem Technol, Hyderabad 500607, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 33期
关键词：
Penifulvin; Ti(III)-mediated epoxide opening; Radical cyclization; Quaternary chiral center; FUNGICOLOUS ISOLATE; RADICAL CYCLIZATION; ELECTRON-TRANSFER; KETONES; REAGENTS;
D O I：
10.1016/j.tetlet.2010.06.076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A trisubstituted alpha,beta-unsaturated ester moiety was suitably placed in a molecule also bearing an epoxy alcohol moiety at as other end to intramolecularly trap the intermediate radical, which was formed when ;the molecule was treated with Cp2T1(111)Cl to regio- and stereoselectively open its epoxy ring, giving rise to a quaternary chiral center The method was subsequently used in an attempt to construct the bicyclic core framework of potent insecticides penifulvins. (C) 2010 Elsevier Ltd All rights ieserved
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收藏
页码：4425 / 4428
页数：4
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