ULTRASONICALLY INDUCED CONJUGATE ADDITION OF IODIDES TO ELECTRON-DEFICIENT OLEFINS AND ITS APPLICATION TO THE SYNTHESIS OF SIDE-CHAIN ANALOGS OF THE HORMONE 1-ALPHA,25-DIHYDROXYVITAMIN-D3

被引：0
作者：
SESTELO, JP
MASCARENAS, JL
CASTEDO, L
MOURINO, A
机构：
[1] UNIV SANTIAGO DE COMPOSTELA, CSIC, DEPT QUIM ORGAN, E-15706 SANTIAGO, SPAIN
[2] UNIV SANTIAGO DE COMPOSTELA, CSIC, SECC ALCALOIDES, E-15706 SANTIAGO, SPAIN
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 01期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A versatile method for the rapid construction of fragments related to the upper part of vitamin D3 from the Lythgoe-Inhoffen diol is described. The key feature of the strategy is a new zinc-copper-induced conjugate addition of iodo triflate 10a to electron-deficient olefins under sonochemical aqueous conditions. These fragments are rapidly and efficiently transformed via the dienyne convergent approach to several derivatives of the hormone 1alpha,25-(OH)2-D3 modified at C-25.
引用
收藏
页码：118 / 123
页数：6
相关论文
共 82 条
[1]   DIFFERENTIATION OF MOUSE MYELOID-LEUKEMIA CELLS INDUCED BY 1-ALPHA,25-DIHYDROXYVITAMIN-D3 [J].
ABE, E ;
MIYAURA, C ;
SAKAGAMI, H ;
TAKEDA, M ;
KONNO, K ;
YAMAZAKI, T ;
YOSHIKI, S ;
SUDA, T .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1981, 78 (08) :4990-4994
[2]   SYNTHETIC ANALOGS OF VITAMIN-D3 WITH AN OXYGEN ATOM IN THE SIDE-CHAIN SKELETON - A TRAIL OF THE DEVELOPMENT OF VITAMIN-D COMPOUNDS WHICH EXHIBIT POTENT DIFFERENTIATION-INDUCING ACTIVITY WITHOUT INDUCING HYPERCALCEMIA [J].
ABE, J ;
MORIKAWA, M ;
MIYAMOTO, K ;
KAIHO, SI ;
FUKUSHIMA, M ;
MIYAURA, C ;
ABE, E ;
SUDA, T ;
NISHII, Y .
FEBS LETTERS, 1987, 226 (01) :58-62
[3]   A SYNTHETIC ANALOG OF VITAMIN-D3, 22-OXA-1-ALPHA,25-DIHYDROXYVITAMIN-D3, IS A POTENT MODULATOR OF INVIVO IMMUNOREGULATING ACTIVITY WITHOUT INDUCING HYPERCALCEMIA IN MICE [J].
ABE, J ;
TAKITA, Y ;
NAKANO, T ;
MIYAURA, C ;
SUDA, T ;
NISHII, Y .
ENDOCRINOLOGY, 1989, 124 (05) :2645-2647
[4]   SYNTHESIS OF 25-HYDROXY-VITAMIN-D3 AND 1-ALPHA,25-DIHYDROXYVITAMIN-D3 FROM VITAMIN-D2 (CALCIFEROL) [J].
ANDREWS, DR ;
BARTON, DHR ;
HESSE, RH ;
PECHET, MM .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4819-4828
[5]   STEREOCONTROLLED TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL [J].
BAGGIOLINI, EG ;
IACOBELLI, JA ;
HENNESSY, BM ;
BATCHO, AD ;
SERENO, JF ;
USKOKOVIC, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3098-3108
[6]   STUDIES OF VITAMIN-D (CALCIFEROL) AND ITS ANALOGS .34. POTENTIAL INHIBITORS OF VITAMIN-D METABOLISM - AN OXA ANALOG OF VITAMIN-D [J].
BARRACK, SA ;
GIBBS, RA ;
OKAMURA, WH .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1790-1796
[7]   SYNTHESIS OF MC-903, A BIOLOGICALLY-ACTIVE VITAMIN-D METABOLITE ANALOG [J].
CALVERLEY, MJ .
TETRAHEDRON, 1987, 43 (20) :4609-4619
[8]   STEROID-RECEPTOR FAMILY - STRUCTURE AND FUNCTIONS [J].
CARSONJURICA, MA ;
SCHRADER, WT ;
OMALLEY, BW .
ENDOCRINE REVIEWS, 1990, 11 (02) :201-220
[9]   PALLADIUM-CATALYZED SYNTHESIS OF DIENYNES RELATED TO VITAMIN-D FROM ENOL TRIFLATES [J].
CASTEDO, L ;
MOURINO, A ;
SARANDESES, LA .
TETRAHEDRON LETTERS, 1986, 27 (13) :1523-1526
[10]   PALLADIUM-CATALYZED SYNTHESIS OF DIENYNES RELATED TO 1-ALPHA,25-DIHYDROXYVITAMIN-D3 [J].
CASTEDO, L ;
MASCARENAS, JL ;
MOURINO, A ;
SARANDESES, LA .
TETRAHEDRON LETTERS, 1988, 29 (10) :1203-1206
123456789