STEREOSPECIFIC SYNTHESIS OF HYDROXYLATED STEROID SIDE-CHAINS - SYNTHESIS OF 25,28-DIHYDROXY-7,8-DIHYDROERGOSTEROL AND ITS C-24 EPIMER VIA [2,3] SIGMATROPIC REARRANGEMENT

被引:29
作者
MIDLAND, MM
KWON, YC
机构
关键词
D O I
10.1016/S0040-4039(01)80841-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
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页码:5017 / 5020
页数:4
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共 22 条
[1]   SELECTIVE REDUCTIONS .37. ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH B-(3-PINANYL)-9-BORABICYCLO[3.3.1]NONANE [J].
BROWN, HC ;
PAI, GG .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1384-1394
[2]   SYNTHESIS OF (24R)-5,28-STIGMASTADIEN-3-BETA-OL AND (24S)-5,28-STIGMASTADIEN-3-BETA-OL AND DETERMINATION OF THE STEREOCHEMISTRY OF THEIR 24 HYDROXY ANALOGS, THE SARINGOSTEROLS [J].
CATALAN, CAN ;
KOKKE, WCMC ;
DUQUE, C ;
DJERASSI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5207-5214
[3]   TRANSITION-METAL-CATALYZED SILYLMETALLATION OF ACETYLENES AND ITS APPLICATION TO THE STEREOSELECTIVE SYNTHESIS OF STEROIDAL SIDE-CHAIN [J].
HAYAMI, H ;
SATO, M ;
KANEMOTO, S ;
MORIZAWA, Y ;
OSHIMA, K ;
NOZAKI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (13) :4491-4492
[4]   STEREOSELECTIVE SYNTHESIS VIA CLAISEN REARRANGEMENTS OF THE MARINE STEROLS OCCELASTEROL, PATINOSTEROL, AND 22,23-DIHYDROOCCELASTEROL [J].
HIRANO, Y ;
DJERASSI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (12) :2420-2426
[5]   STEREOSELECTIVE INTRODUCTION OF HYDROXY-GROUPS INTO THE CHOLESTEROL SIDE-CHAIN - PREPARATION OF (24R)-24,25-DIHYDROXYVITAMIN-D3 AND (24S)-24,25-DIHYDROXYVITAMIN-D3 AND (25R)-25,26-DIHYDROXYVITAMIN-D3 AND (25S)-25,26-DIHYDROXYVITAMIN-D3 BY ASYMMETRIC-SYNTHESIS [J].
KOIZUMI, N ;
ISHIGURO, M ;
YASUDA, M ;
IKEKAWA, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (07) :1401-1410
[6]   CHIRALITY TRANSFER IN THE [2,3] WITTIG REARRANGEMENT [J].
MARSHALL, JA ;
JENSON, TM .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (10) :1707-1712
[7]  
MIDLAND MM, 1984, TETRAHEDRON, V40, P1371
[8]   STEREOCONTROLLED SYNTHESIS OF STEROID SIDE-CHAINS VIA ORGANOBORANES - STEREOSPECIFIC SYNTHESIS OF 20R-HYDROXYCHOLESTEROL AND 20S-25-HYDROXYCHOLESTEROL [J].
MIDLAND, MM ;
KWON, YC .
TETRAHEDRON LETTERS, 1982, 23 (20) :2077-2080
[10]   REDUCTION OF ALPHA,BETA-ACETYLENIC KETONES WITH B-3-PINANYL-9-BORABICYCLO[3.3.1]NONANE - HIGH ASYMMETRIC INDUCTION IN ALIPHATIC SYSTEMS [J].
MIDLAND, MM ;
MCDOWELL, DC ;
HATCH, RL ;
TRAMONTANO, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :867-869