Studies on the synthesis of reidispongiolide A: stereoselective synthesis of the C(22)-C(36) fragment

被引：7

作者：

Ying, Maben ^{[1
]}

Roush, William R. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, Jupiter, FL 33458 USA

来源：

TETRAHEDRON | 2011年 / 67卷 / 52期

基金：

美国国家卫生研究院;

关键词：

Studies on the synthesis of reidispongiolide A; Mismatched double asymmetric crotylboration; Stereoselective synthesis of the anti; anti stereotriad; POTENT CYTOTOXIC MACROLIDES; STEREOCHEMICAL ASSIGNMENT; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; SIMPLIFIED ANALOGS; ALCOHOLS; HYDROBORATION; SPHINXOLIDES; STEREOTRIAD; REDUCTION;

D O I：

10.1016/j.tet2011.10.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective synthesis of the C(22)-C(36) fragment 2 of reidispongiolide A is described. This synthesis features the highly stereoselective mismatched double asymmetric crotylboration reaction of the aldehyde derived from 5 and the new chiral reagent (S)-(E)-7 that provides 12 with >15:1dr. Subsequent coupling of the derived vinyl iodide 3 with aldehyde 16 provided allylic alcohol 17, that was elaborated by three steps into the targeted reidispongiolide fragment 2. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：10274 / 10280

页数：7

共 38 条

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