5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings

被引：3

作者：

Bjelakovic, Mira S. ^{[1
]}

Krstic, Natalija M. ^{[1
]}

Todorovic, Nina ^{[1
]}

Krunic, Aleksej ^{[2
]}

Tinant, Bernard ^{[3
]}

Dabovic, Milan M. ^{[1
]}

Pavlovic, Vladimir D. ^{[1
,4
]}

机构：

[1] ICTM, Ctr Chem, Belgrade 11001, Serbia

[2] UIC Coll Pharm, Dept Med Chem & Pharmacognosy, Chicago, IL USA

[3] Catholic Univ Louvain, Dept Chem, B-1348 Louvain, Belgium

[4] Univ Belgrade, Fac Chem, Belgrade 11001, Serbia

来源：

TETRAHEDRON | 2009年 / 65卷 / 46期

关键词：

5; alpha; 14 alpha-Dihydroxycholestan-3 beta-yl acetate; Oxidative beta-fragmentation; 5,10:13,14-Disecosteroids; Hypoiodite reagent; 2D NMR spectroscopy; MEDIUM-SIZED RING; IRREVERSIBLE INACTIVATION; X-RAY; CONFORMATIONS; 5,10-SECOSTEROIDS; SECOSTEROIDS; NMR; 10-SECOSTEROIDS; REACTIVITY;

D O I：

10.1016/j.tet.2009.09.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper a synthetic pathway to the modified 5,10 13,14-bisfragmentation cholestane derivatives 8-14 is described. The synthesis involves introduction of the 5 alpha- and 14 alpha-hydroxyl groups in the cholestane molecule and Subsequent cleavage of the C(5)-C(10) bond in 5 alpha,14 alpha-dihydroxycholestan-3 beta-yl acetate (4) with the HgO/I-2 reagent and the C(13)-C( 14) bond in the stereoisomeric 14 alpha-hydroxy-5,10-secosteroids 5 and 6 with the Pb(OAc)(4)/I-2 reagent Complete and Unambiguous H-1 and C-13 NMR resonance assignments of the obtained secosteroids. as well as the Solution conformations of then 10- and 9-membered rings were determined by extensive analysis of 1D and 2D NMR spectral data The structures and the solid-state conformations of 5,10-secosteroids 5-7 were confirmed by X-ray analysis All diseco-compounds have a novel 5.10 13,14-disecocholestane skeleton. (C) 2009 Elsevier Ltd. All rights reserved

引用

页码：9557 / 9568

页数：12

共 33 条

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