CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF (3S)-2,3-OXIDOSQUALENE

被引:24
作者
COREY, EJ
YI, KY
MATSUDA, SPT
机构
关键词
D O I
10.1016/S0040-4039(00)74200-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and simple enantioselective process is described for the synthesis of (3S)-2,3-oxidosqualene (1) which provides this valuable compound contaminated with only 4% of the R enantiomer. The synthesis employs a chiral catalyst which is efficiently recovered for reuse.
引用
收藏
页码:2319 / 2322
页数:4
相关论文
共 26 条
[1]  
ABDALLAH MA, 1975, J CHEM SOC PERK T 1, P888
[2]   RESOLUTION OF 2,3-DIHYDROSQUALENE-2,3-DIOL, 10,11-DIHYDRO-10,11-DIHYDROXYFARNESYL BENZOATE, AND 6,7-DIHYDRO-6,7-DIHYDROXYGERANYL BENZOATE - SYNTHESIS OF (3R)-2,3 ETC (FILL OUT) AND (3S)-2,3-EPOXY-2,3-DIHYDROSQUALENE [J].
BOAR, RB ;
DAMPS, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (06) :709-712
[3]   METABOLIC FATE OF 10,11-DIHYDROSQUALENE IN STEROL-PRODUCING RAT LIVER HOMOGENATE [J].
COREY, EJ ;
RUSSEY, WE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (20) :4751-&
[4]   2,3-OXIDOSQUALENE AN INTERMEDIATE IN BIOLOGICAL SYNTHESIS OF STEROLS FROM SQUALENE [J].
COREY, EJ ;
RUSSEY, WE ;
DEMONTEL.PR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (20) :4750-&
[5]   AN EFFECTIVE SYSTEM FOR EPOXIDE-INITIATED CATION-OLEFIN CYCLIZATION [J].
COREY, EJ ;
SODEOKA, M .
TETRAHEDRON LETTERS, 1991, 32 (48) :7005-7008
[6]   AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].
COREY, EJ ;
SHIBATA, S ;
BAKSHI, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863
[7]   A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS AND DEUTERATED PRIMARY ALCOHOLS BY CARBONYL REDUCTION [J].
COREY, EJ ;
LINK, JO .
TETRAHEDRON LETTERS, 1989, 30 (46) :6275-6278
[8]   A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].
COREY, EJ ;
BAKSHI, RK .
TETRAHEDRON LETTERS, 1990, 31 (05) :611-614
[9]   AN EXPERIMENTAL DEMONSTRATION OF THE STEREOCHEMISTRY OF ENZYMATIC CYCLIZATION OF 2,3-OXIDOSQUALENE TO THE PROTOSTEROL SYSTEM, FORERUNNER OF LANOSTEROL AND CHOLESTEROL [J].
COREY, EJ ;
VIRGIL, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :4025-4026
[10]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF A PROTOSTEROL, 3-BETA,20-DIHYDROXYPROTOST-24-ENE [J].
COREY, EJ ;
VIRGIL, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6429-6431