An enantioselective approach to the Securinega alkaloids: the total synthesis of (+)-norsecurinine and (+)-allonorsecurinine

被引：21
|
作者：
Medeiros, Matthew R. [2 ]
Wood, John L. [1 ]
机构：
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[2] Yale Univ, Dept Chem, New Haven, CT 06520 USA
来源：
TETRAHEDRON | 2010年 / 66卷 / 26期
关键词：
Securinga Alkaloids; Norsecurinine; Allonorsecrinine; Total Synthesis; Rhodium Carbenoid; Claisen rearrangement; INITIATED CLAISEN REARRANGEMENT; CARBENOID MEDIATED CYCLIZATIONS; DISCOIDES MUELL ARG; EFFICIENT SYNTHESIS; PHYLLANTHUS-NIRURI; (-)-NORSECURININE; ALCOHOLS; VIROSA; VIROALLOSECURININE; VIROSECURININE;
D O I：
10.1016/j.tet.2010.03.015
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Total syntheses of (+)-norsecurinine and (+)-allonorsecurinine are described that utilize a rhodium carbenoid-initiated O-H insertion/Claisen rearrangement/1,2-allyl migration domino process for the stereoselective introduction of the tertiary alcohol moiety. Overall the employed strategy is flexible and will allow access to other members of the Securinega family of alkaloids. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4701 / 4709
页数：9
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