A short convergent synthesis of the side chains of brassinolide, cathasterone, and cryptolide

被引：4
作者：
Hurski, Alaksiej [1 ]
Zhabinskii, Vladimir [1 ]
Khripach, Vladimir [1 ]
机构：
[1] Natl Acad Sci Belarus, Inst Bioorgan Chem, Minsk 220141, BELARUS
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 06期
关键词：
Brassinosteroids; Thioacetal-containing chiral synthon; Side chain construction; PLANT-GROWTH REGULATOR; STEREOSELECTIVE-SYNTHESIS; FORMAL SYNTHESIS; STEREOCONTROLLED SYNTHESIS; CONSTRUCTION; INTERMEDIATE; STEROIDS; ANALOGS; ROUTE;
D O I：
10.1016/j.tetlet.2012.11.094
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new approach to steroidal derivatives of the campestane series, containing the 22 alpha-hydroxy-, 22 alpha,23 alpha-dihydroxy-, and 22 alpha-hydroxy-23-ketone moieties characteristic of brassinolide and its congeners, has been developed. The key step is the coupling of a steroidal C-22 aldehyde with an anion derived from a specially synthesized thioacetal-containing chiral synthon. The cathasterone and cryptolide side chains are prepared by reductive or hydrolytic thioketal removal, respectively. The brassinolide side chain is obtained by DIBAL-H reduction of the TBS-protected 22 alpha-hydroxy-23-ketone. (c) 2012 Elsevier Ltd. All rights reserved.
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页码：584 / 586
页数：3
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