PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS BY USING ENZYMES .13. A SYNTHETIC STUDY OF (-)-DIHYDROEDULAN-II AND RELATED-COMPOUNDS

被引：15

作者：

SUGAI, T ^{[1
]}

YOKOCHI, T ^{[1
]}

WATANABE, N ^{[1
]}

OHTA, H ^{[1
]}

机构：

[1] KEIO UNIV,DEPT CHEM,HIYOSHI 3-14-1,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

TETRAHEDRON | 1991年 / 47卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)89725-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Dihydroedulan II and related compounds were synthesized from (2R,1'Rs)-dihydro-alpha-ionol, which was prepared by lipase-catalyzed enantioselective transesterification of the corresponding diastereomeric mixture as the key-step. Fungal allylic oxidation of (-)-dihydroedulan II worked well to afford a corresponding alcohol as well as (+)-dihydroedulan-8-one.

引用

页码：7227 / 7236

页数：10

共 19 条

[1] ISOLATION, TENTATIVE IDENTIFICATION, AND SYNTHESIS STUDIES OF VOLATILE COMPONENTS OF HAIRPENCIL SECRETION OF MONARCH BUTTERFLY
BELLAS, TE
BROWNLEE, RG
SILVERSTEIN, RM
[J]. TETRAHEDRON, 1974, 30 (15) : 2267 - 2271
[2] GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES
CHEN, CS
SIH, CJ
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06): : 695 - 707
[3] QUALITATIVE EVALUATION OF AROMATIC HERBS BY DIRECT HEADSPACE GC ANALYSIS - APPLICATIONS OF THE METHOD AND COMPARISON WITH THE TRADITIONAL ANALYSIS OF ESSENTIAL OILS
CHIALVA, F
GABRI, G
LIDDLE, PAP
ULIAN, F
[J]. JOURNAL OF HIGH RESOLUTION CHROMATOGRAPHY & CHROMATOGRAPHY COMMUNICATIONS, 1982, 5 (04): : 182 - 188
[4] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 512 - 519
[5] SYNTHESIS AND CHIRALITY OF (5R,6R)-5,6-DIHYDRO-BETA,PSI-CAROTENE-5,6-DIOL, (5R,6R,6'R)-5,6-DIHYDRO-BETA,EPSILON-CAROTENE-5,6-DIOL, (5S,6R)-5,6-EPOXY-5,6-DIHYDRO-BETA,PSI-CAROTENE AND (5S,6R6'R)-5,6-EPOXY-5,6-DIHYDRO-BETA,EPSILON-CAROTENE
ESCHENMOSER, W
UEBELHART, P
EUGSTER, CH
[J]. HELVETICA CHIMICA ACTA, 1979, 62 (08) : 2534 - 2538
[6] TERPENOIDS FROM BARK BEETLES, SOLITARY BEES AND DANAINE BUTTERFLIES
FRANCKE, W
BARTELS, J
KROHN, S
SCHULZ, S
BAADER, E
TENGO, J
SCHNEIDER, D
[J]. PURE AND APPLIED CHEMISTRY, 1989, 61 (03) : 539 - 542
[7] FRANCKE W, 1990, LIEBIGS ANN CHEM, P1195
[8] SYNTHESIS OF (-)-(R)-4-HYDROXY-BETA-IONONE AND (-)-(5R,6S)-5-HYDROXY-4,5-DIHYDRO-ALPHA-IONONE FROM (-)-(S)-ALPHA-IONONE
HAAG, A
ESCHENMOSER, W
EUGSTER, CH
[J]. HELVETICA CHIMICA ACTA, 1980, 63 (01) : 10 - 15
[9] PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS BY USING ENZYMES .10. BIOCHEMICAL PREPARATION OF OPTICALLY-ACTIVE 4-HYDROXY-BETA-IONONE AND ITS TRANSFORMATION TO (S)-6-HYDROXY-ALPHA-IONONE
KAKEYA, H
SUGAI, T
OHTA, H
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (07): : 1873 - 1876
[10] MASSIMO M, 1986, PLANTA MED, P187

← 1 2 →