NOVEL ROUTE TO SOME BIOLOGICALLY IMPORTANT COMPOUNDS STARTING WITH A COMMON CHIRAL, BICYCLIC, FUSED LACTONE - ENANTIOSELECTIVE SYNTHESIS OF (-)-BOSCHNIALACTONE AND 2 ANTITHROMBOTICS

被引：21

作者：

ARAI, Y ^{[1
]}

KAWANAMI, S ^{[1
]}

KOIZUMI, T ^{[1
]}

机构：

[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,SUGITANI 2630,SUGITANI,TOYAMA 93001,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 12期

关键词：

D O I：

10.1039/p19910002969

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three biologically important compounds, (-)-boschnialactone and the antithrombotics (+)- and (-)-(5Z)-6-{(1S,4R)-3-endo-(4-chlorophenylsulphonylamino)bicyclo[2.2.1]hept-5-en-2-endo- and exo-yl}hex-5-enoic acid have been synthesized starting from a common chiral lactone which is easily available via an asymmetric Diels-Alder reaction.

引用

页码：2969 / 2975

页数：7

共 36 条

[1] CATALYTIC ASYMMETRIC RING-OPENING OF BRIDGED TRICYCLIC ANHYDRIDES
AITKEN, RA
GOPAL, J
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (08) : 517 - 520
[2] ENANTIOSELECTIVE SYNTHESIS OF (-)-BOSCHNIALACTONE
ARAI, Y
KAWANAMI, S
KOIZUMI, T
[J]. CHEMISTRY LETTERS, 1990, (09) : 1585 - 1586
[3] AN ENANTIODIVERGENT SYNTHESIS OF FUSED BICYCLO[2.2.1]HEPTANE LACTONES VIA AN ASYMMETRIC DIELS-ALDER REACTION
ARAI, Y
MATSUI, M
KOIZUMI, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04): : 1233 - 1234
[4] SYNTHESIS OF TERREIN, A METABOLITE OF ASPERGILLUS-TERREUS
AUERBACH, J
WEINREB, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (08) : 298 - 299
[5] AN EXPEDIENT AND STEREOSELECTIVE SYNTHESIS OF (+0-) BOSCHNIALACTONE
CAILLE, JC
TABYAOUI, B
GUILARD, R
BELLAMY, FD
[J]. SYNTHETIC COMMUNICATIONS, 1985, 15 (08) : 669 - 674
[6] IRIDOIDS - STEREOSPECIFIC SYNTHESIS OF FUNCTIONALIZED CYCLOPENTANOID INTERMEDIATES VIA BICYCLO[2.2.1]HEPTANONES
CALLANT, P
STORME, P
VANDEREYCKEN, E
VANDEWALLE, M
[J]. TETRAHEDRON LETTERS, 1983, 24 (51) : 5797 - 5800
[7] TRICYCLO[3.3.0.02,8]OCTAN-3-ONES - PHOTOCHEMICALLY PREPARED BUILDING-BLOCKS FOR ENANTIOSPECIFIC TOTAL SYNTHESES OF CYCLOPENTANOID NATURAL-PRODUCTS
DEMUTH, M
SCHAFFNER, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1982, 21 (11) : 820 - 836
[8] EMINWALD J, 1968, J AM CHEM SOC, V90, P3218
[9] FUJIMOTO Y, 1976, TETRAHEDRON LETT, P3325
[10] FURUICHI K, 1974, TETRAHEDRON LETT, P3685

← 1 2 3 4 →