Toward the Total Synthesis of the Brasilinolides: Construction of a Differentially Protected C20-C38 Segment

被引：15

作者：

Paterson, Ian ^{[1
]}

Burton, Paul M. ^{[1
]}

Cordier, Christopher J. ^{[1
]}

Housden, Michael P. ^{[1
]}

Muehlthau, Friedrich A. ^{[1
]}

Loiseleur, Olivier ^{[2
]}

机构：

[1] Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England

[2] Syngenta Crop Protect AG, CH-4332 Stein, Switzerland

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 03期

基金：

英国工程与自然科学研究理事会;

关键词：

NOCARDIA-BRASILIENSIS; IMMUNOSUPPRESSIVE MACROLIDE; PRACTICAL SYNTHESIS; KINETIC RESOLUTION; NATURAL-PRODUCTS; REDUCTION; EFFICIENT; KETONES;

D O I：

10.1021/ol802769e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, convergent synthesis of a differentially protected C20-C38 segment of the brasilinolides is described. Iterative 1,4-syn aldol additions and ketone reductions were employed to construct the two related stereotetrads, while a sequence of Horner-Wadsworth-Emmons (HWE) coupling, CBS reduction, and Sharpless AE installed the epoxy alcohol functionality.

引用

收藏

页码：693 / 696

页数：4

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