Synthesis of 22-oxaspiro[4.5]decane CD-ring modified analogs of 1α,25-dihydroxyvitamin D3

被引:7
作者
De Buysser, Frederik [1 ]
Verlinden, Lieve [2 ]
Verstuyf, Annemieke [2 ]
De Clercq, Pierre J. [1 ]
机构
[1] Univ Ghent, Dept Organ Chem, B-9000 Ghent, Belgium
[2] Catholic Univ Louvain, Lab Expt Med & Endocrinol, B-3000 Louvain, Belgium
关键词
Spirocyclic decanones; Calcitriol analogs; Enantioselective synthesis; VITAMIN-D; ENANTIOMERICALLY PURE; BIOLOGICAL-ACTIVITY; CATALYZED-REACTIONS;
D O I
10.1016/j.tetlet.2009.05.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In search of analogs of 1 alpha,25-dihydroxyvitamin D-3 featuring a dissociation of calcemic and other activities, a series of stereoisomeric 19-nor-22-oxa derivatives, characterized by a spiro[4.5]decane cyclic system instead of the classical CD-ring system, have been synthesized in an enantioselective way. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4174 / 4177
页数:4
相关论文
共 29 条
[1]   RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].
ADAMS, J ;
SPERO, DM .
TETRAHEDRON, 1991, 47 (10-11) :1765-1808
[2]   A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions [J].
Arai, T ;
Sasai, H ;
Aoe, K ;
Okamura, K ;
Date, T ;
Shibasaki, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :104-106
[3]   20-EPI-VITAMIN-D3 ANALOGS - A NOVEL CLASS OF POTENT REGULATORS OF CELL-GROWTH AND IMMUNE-RESPONSES [J].
BINDERUP, L ;
LATINI, S ;
BINDERUP, E ;
BRETTING, C ;
CALVERLEY, M ;
HANSEN, K .
BIOCHEMICAL PHARMACOLOGY, 1991, 42 (08) :1569-1575
[4]   STRUCTURE-FUNCTION-RELATIONSHIPS IN THE VITAMIN-D ENDOCRINE SYSTEM [J].
BOUILLON, R ;
OKAMURA, WH ;
NORMAN, AW .
ENDOCRINE REVIEWS, 1995, 16 (02) :200-257
[5]   Thirteenth Workshop on Vitamin D [J].
Bouillon, Roger ;
Norman, Anthony W. ;
Pasqualini, Jorge R. .
JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2007, 103 (3-5) :201-203
[6]   Synthesis of new 18-substituted analogues of calcitriol using a photochemical remote functionalization [J].
Cornella, I ;
Sestelo, JP ;
Mouriño, A ;
Sarandeses, LA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4707-4714
[7]  
DAI HY, 1994, SYNTHESIS-STUTTGART, P1383
[8]   The development of CD-ring modified analogs of 1α,25-dihydroxyvitamin D [J].
De Clercq, Pierre J. ;
De Buysser, Frederik ;
Minne, Garrett ;
Schepens, Wim ;
Vrielynck, Freek ;
Van Haver, Dirk ;
Vandewalle, Maurits ;
Verstuyf, Annemieke ;
Bouillon, Roger .
JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2007, 103 (3-5) :206-212
[9]  
Kirmse W, 2002, EUR J ORG CHEM, V2002, P2193
[10]   Recent synthetic applications of the dealkoxycarbonylation reaction. Part 1. Dealkoxycarbonylations of malonate esters [J].
Krapcho, A. Paul .
ARKIVOC, 2007, :1-53