Synthesis of "glycospirostanes" via ring-closing metathesis

被引：12

作者：

Czajkowska, Dorota ^{[1
]}

Morzycki, Jacek W. ^{[1
]}

Santillan, Rosa ^{[2
]}

Siergiejczyk, Leszek ^{[1
]}

机构：

[1] Univ Bialystok, Inst Chem, PL-15443 Bialystok, Poland

[2] Inst Politecn Nacl, Dept Quim, Ctr Invest & Estudios Avanzados, Mexico City 07000, DF, Mexico

来源：

STEROIDS | 2009年 / 74卷 / 13-14期

关键词：

Glycospirostanes; Ring-closing metathesis; Polyhydroxylated compounds; TRITERPENOID SAPONINS; BIOLOGICAL-ACTIVITIES; SAPOGENINS;

D O I：

10.1016/j.steroids.2009.09.001

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Syntheses of "glycospirostanes" from 3 beta-hydroxy-23,24-dinor-5 alpha-cholano-22,16-lactone and 3 alpha-hydroxy-23,24-dinor-5 beta- -cholano-22,16-lactone were performed. The key step of these syntheses was ring-closing metathesis of the corresponding C,O-diallyl derivative. Further elaboration of the six-membered ring F consisted of allylic hydroxylation with SeO(2) followed by OsO(4) dihydroxylation of the C24-C25 double bond. The obtained final products proved to be simultaneously O- and C-L-arabinopyranosides. (C) 2009 Elsevier Inc. All rights reserved.

引用

页码：1073 / 1079

页数：7

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