Symmetry in the synthesis of the A-ring of a vitamin D hybrid analogue with significant transactivation activity: A combinatorial sequence of regioselective propiolate-ene, catalytic enantioselective epoxidation and carbonyl-ene cyclization reactions

被引:38
作者
Mikami, K
Osawa, A
Isaka, A
Sawa, E
Shimizu, M
Terada, M
Kubodera, N
Nakagawa, K
Tsugawa, N
Okano, T
机构
[1] Tokyo Inst Technol, Dept Chem Technol, Tokyo 152, Japan
[2] Chugai Pharmaceut Co Ltd, Chuo Ku, Tokyo 104, Japan
[3] Kobe Pharmaceut Univ, Dept Hyg Sci, Higashinada Ku, Kobe 658, Hyogo, Japan
关键词
D O I
10.1016/S0040-4039(98)00272-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The combination of the regioselective propiolate-ene reaction, catalytic enantioselective epoxidation and catalytic enantioselective carbonyl-ene cyclization completes the synthesis of the A ring of the hybrid 19-nor-22-era D-3 analogue (1), which shows the significant activity in transactivation. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3359 / 3362
页数:4
相关论文
共 49 条
[1]  
[Anonymous], 1992, Org. Synth
[2]  
Baba S., 1994, B SOC CHIM FR, V131, P525
[3]   STRUCTURE-FUNCTION-RELATIONSHIPS IN THE VITAMIN-D ENDOCRINE SYSTEM [J].
BOUILLON, R ;
OKAMURA, WH ;
NORMAN, AW .
ENDOCRINE REVIEWS, 1995, 16 (02) :200-257
[4]  
DAI HY, 1994, SYNTHESIS-STUTTGART, P1383
[5]  
ETTINGER RA, 1985, VITAMIN D CHEM BIOCH
[6]  
ETTINGER RA, 1996, ADV DRUG RES, V28, P269
[7]   PHAGOCYTIC-CELLS SYNTHESIZE 19-NOR-10-KETO-25-HYDROXYVITAMIN-D3, A METABOLITE THAT MAY INDUCE DIFFERENTIATION OF THE HUMAN MONOBLASTIC CELL-LINE U937 [J].
GRAY, TK ;
MILLINGTON, DS ;
MALTBY, DA ;
WILLIAMS, ME ;
COHEN, MS ;
DODD, RC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1985, 82 (23) :8218-8221
[8]   SYNTHESIS OF ERYTHRO-D-4-PENTENETRIOLS AND ERYTHRO-L-4-PENTENETRIOLS - SELECTIVE EPOXY ALLYL ALCOHOL HYDROLYSIS WITH RETENTION OR TWOFOLD INVERSION (ENANTIOMERIZATION) [J].
HAFELE, B ;
SCHROTER, D ;
JAGER, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (01) :87-89
[9]   PREPARATION OF (2R,3S)-1,2-EPOXYPENT-4-EN-3-OL, A NEW CHIRAL BUILDING BLOCK FOR THE SYNTHESIS OF (+)-ENDO-BREVICOMIN AND (-)-EXO-BREVICOMIN [J].
HATAKEYAMA, S ;
SAKURAI, K ;
TAKANO, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (24) :1759-1761
[10]   ENE REACTION [J].
HOFFMANN, HM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) :556-&