Studies directed towards the total synthesis of koshikalide: stereoselective synthesis of the macrocyclic core

被引：16
|
作者：
Venkanna, Arramshetti [1 ]
Sreedhar, Eppakayala [1 ]
Siva, Bandi [1 ]
Babu, Katragadda Suresh [1 ]
Prasad, Kothakonda Rajendra [1 ]
Rao, Janaswamy Madhusudana [1 ]
机构：
[1] CSIR, Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500607, Andhra Pradesh, India
来源：
TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 17期
关键词：
FORMAL TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ROUTE; REAGENTS; TOXIN;
D O I：
10.1016/j.tetasy.2013.07.002
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The stereoselective synthesis of the macrolactone core of the natural product koshikalide is described. Starting with readily available 1,4-butanediol and malic acid as synthons, our synthetic strategy involved the reiterative application of Gilman's reaction, Swem oxidation and Sharpless asymmetric epoxidation to establish the required stereocentres. Other key steps in the synthesis include Negishi cross coupling and Horner-Wadsworth-Emmons (HWE) reactions for construction of the main fragments. The 14-membered lactone ring was prepared by a selective Mitsunobu macrolactonization approach. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1010 / 1022
页数：13
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