EXPEDIENT PREPARATION AND ENANTIOMERIZATION OF OPTICALLY PURE DICYCLOPENTADIENONE (TRICYCLO[5.2.1.0(2,6)]DECA-4,8-DIEN-3-ONE)

被引：44

作者：

TAKANO, S

INOMATA, K

TAKAHASHI, M

OGASAWARA, K

机构：

[1] Pharmaceutical Institute, Tohoku University, Aobayama, Sendai

来源：

SYNLETT | 1991年 / 09期

关键词：

D O I：

10.1055/s-1991-20823

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Expedient synthesis of optically pure (+)- and (-)-enantiomers of dicyclopentadienone (1; tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one) has been developed via the asymmetric resolution of the corresponding dienol mediated by lipase in organic solvents. The interconversion (enantiomerization) of both enantiomers has also been achieved by employing the Wharton reaction.

引用

页码：636 / 638

页数：3

共 17 条

[1] PREPARATIVE PRODUCTION OF OPTICALLY-ACTIVE ESTERS AND ALCOHOLS USING ESTERASE-CATALYZED STEREOSPECIFIC TRANS-ESTERIFICATION IN ORGANIC MEDIA
CAMBOU, B
KLIBANOV, AM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (09) : 2687 - 2692
[2] STUDIES IN THE SYNTHESIS OF THE THROMBOXANE RECEPTOR ANTAGONIST EP-092 AND ITS ENANTIOMERS
GARLAND, RB
MIYANO, M
PIREH, D
CLARE, M
FINNEGAN, PM
SWENTON, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) : 5854 - 5861
[3] RESOLUTION OF RACEMIC MIXTURES VIA LIPASE CATALYSIS IN ORGANIC-SOLVENTS
KIRCHNER, G
SCOLLAR, MP
KLIBANOV, AM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) : 7072 - 7076
[4] KLIVANOV AM, 1990, ACCOUNTS CHEM RES, V23, P114
[5] ENZYMATIC OPTICAL RESOLUTION AND ABSOLUTE-CONFIGURATION OF TRICYCLO[5.2.1.02,6]DECADIENONES
KLUNDER, AJH
HUIZINGA, WB
HULSHOF, AJM
ZWANENBURG, B
[J]. TETRAHEDRON LETTERS, 1986, 27 (22) : 2543 - 2546
[6] KLUNDER AJH, 1991, TETRAHEDRON LETT, V26, P3131
[7] ABSOLUTE-CONFIGURATIONS OF CYTO-TOXIC MARINE CEMBRANOLIDES - CONSIDERATION OF MOSHERS METHOD
KUSUMI, T
OHTANI, I
INOUYE, Y
KAKISAWA, H
[J]. TETRAHEDRON LETTERS, 1988, 29 (37) : 4731 - 4734
[8] ROSENBLUM M, 1957, J AM CHEM SOC, V79, P3170
[9] SYNTHESES OF OPTICALLY-ACTIVE PENTAACETATES OF PSEUDO-BETA-L-ALLOPYRANOSE AND PSEUDO-ALPHA-D-MANNOPYRANOSE
TADANO, K
FUKABORI, C
MIYAZAKI, M
KIMURA, H
SUAMI, T
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) : 2189 - 2196
[10] ENANTIODIVERGENT ROUTE TO BOTH ENANTIOMERS OF BETA-SANTALENE AND EPI-BETA-SANTALENE FROM A SINGLE CHIRAL TEMPLATE
TAKANO, S
INOMATA, K
KUROTAKI, A
OHKAWA, T
OGASAWARA, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (22) : 1720 - 1722

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