SYNTHESIS AND UTILIZATION OF OPTICALLY-ACTIVE 2-SUBSTITUTED 4-(TRIMETHYLSILYL)CYCLOPENTANONES - SYNTHESIS OF (-)-MASSOIALACTONE AND (+)-BETA-CUPARENONE

被引：32

作者：

ASAOKA, M

HAYASHIBE, S

SONODA, S

TAKEI, H

机构：

[1] Department of Life Chemistry, Tokyo Institute of Technology, Midoriku, Yokohama

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 33期

关键词：

D O I：

10.1016/S0040-4039(00)97727-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring contraction by BF3 ·Et2O catalyzed epoxide rearrangement of 3-substituted 5-trimethylsilyl-2,3-epoxycyclohexanones gave the corresponding 2-substituted 4-(trimethylsilyl)cyclopentanones diastereoselectively. Synthesis of (-)-massoialactone and (+)-β-cuparenone utilizing the above transformation is also described. © 1990.

引用

页码：4761 / 4764

页数：4

共 14 条

[1] CONSTRUCTION OF CHIRAL QUARTERNARY CARBON CENTERS USING 3-SUBSTITUTED 5-TRIMETHYLSILYL-2-CYCLOHEXENONES - SYNTHESIS OF (+)-ALPHA-CUPARENONE
ASAOKA, M
TAKENOUCHI, K
TAKEI, H
[J]. TETRAHEDRON LETTERS, 1988, 29 (03) : 325 - 328
[2] SYNTHESIS OF (+)-ALPHA-CURCUMENE, (+)-CURCUMONE, AND (-)-METHYL CITRONELLATE STARTING FROM OPTICALLY PURE 5-TRIMETHYLSILYL-2-CYCLOHEXENONE
ASAOKA, M
SHIMA, K
FUJII, N
TAKEI, H
[J]. TETRAHEDRON, 1988, 44 (15) : 4757 - 4766
[3] ASAOKA M, 1990, YUKI GOSEI KAGAKU KY, V48, P216
[4] BENNETT F, 1989, HETEROCYCLES, V29, P639
[5] INSECT VENOMS ATTRACTANTS AND REPELLENTS .11. MASSOILACTONE FROM 2 SPECIES OF FORMICINE ANTS AND SOME OBSERVATIONS ON CONSTITUENTS OF BARK OIL OF CRYPTOCARYA MASSOIA
CAVILL, GWK
CLARK, DV
WHITFIELD, FB
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1968, 21 (11) : 2819 - +
[6] CHETTY GL, 1964, TETRAHEDRON LETT, P73
[7] ENANTIOSELECTIVE RING CONSTRUCTION THROUGH ASYMMETRIC OLEFIN-KETENE CYCLOADDITION - A HIGHLY ENANTIOCONTROLLED APPROACH TO (-)-ALPHA-CUPARENONE AND (+)-BETA-CUPARENONE
GREENE, AE
CHARBONNIER, F
LUCHE, MJ
MOYANO, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) : 4752 - 4753
[8] KAISER R, 1976, TETRAHEDRON LETT, P1659
[9] ABSOLUTE-CONFIGURATION OF (-)-MASSOILACTONE AS CONFIRMED BY A SYNTHESIS OF ITS (S)-(+)-ISOMER
MORI, K
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1976, 40 (08): : 1617 - 1619
[10] ENANTIOMERICALLY PURE LACTONES .3. SYNTHESIS OF AND STEREOSPECIFIC CONJUGATE ADDITIONS TO ALPHA,BETA-UNSATURATED LACTONES
PIRKLE, WH
ADAMS, PE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) : 4117 - 4121

← 1 2 →