ASYMMETRIC-SYNTHESIS OF (-)-(1R,2S)-CISPENTACIN AND RELATED CIS-2-AMINO AND TRANS-2-AMINO CYCLOPENTANE-1-CARBOXYLIC AND CYCLOHEXANE-1-CARBOXYLIC ACIDS

被引：90

作者：

DAVIES, SG

ICHIHARA, O

LENOIR, I

WALTERS, IAS

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 11期

关键词：

D O I：

10.1039/p19940001411

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The antifungal antibiotic (-)-(1R,2S)-2-aminocyclopentane-1-carboxylic acid (cispentacin) 8 and its cyclohexane homologue 14 have been prepared utilizing the highly stereoselective conjugate addition of homochiral lithium N-benzyl-N-alpha-methylbenzylamide 5. The corresponding trans-beta-amino acids 10 and 16 were also prepared via the selective epimerization of the cis-beta-amino ester conjugate addition products.

引用

页码：1411 / 1415

页数：5

共 20 条

[11] BETA-AMINO ACIDS - MAMMALIAN METABOLISM AND UTILITY AS ALPHA-AMINO-ACID ANALOGS
GRIFFITH, OW
[J]. ANNUAL REVIEW OF BIOCHEMISTRY, 1986, 55 : 855 - 878
[12] IWAMOTO T, 1990, J ANTIBIOT, V43, P1
[13] SYNTHESIS AND STRUCTURE DETERMINATION OF FR109615, A NEW ANTIFUNGAL ANTIBIOTIC
KAWABATA, K
INAMOTO, Y
SAKANE, K
IWAMOTO, T
HASHIMOTO, S
[J]. JOURNAL OF ANTIBIOTICS, 1990, 43 (05) : 513 - 518
[14] CISPENTACIN, A NEW ANTIFUNGAL ANTIBIOTIC .1. PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND STRUCTURE
KONISHI, M
NISHIO, M
SAITOH, K
MIYAKI, T
OKI, T
KAWAGUCHI, H
[J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (12) : 1749 - 1755
[15] KONOSU T, 1993, CHEM PHARM BULL, V41, P1012
[16] KRICHELDORF HR, 1975, LIEBIGS ANN CHEM, P1387
[17] SYNTHESIS AND ANTIFUNGAL ACTIVITY OF FR109615-ANALOGS
OHKI, H
INAMOTO, Y
KAWABATA, K
KAMIMURA, T
SAKANE, K
[J]. JOURNAL OF ANTIBIOTICS, 1991, 44 (05) : 546 - 549
[18] CISPENTACIN, A NEW ANTIFUNGAL ANTIBIOTIC .2. INVITRO AND INVIVO ANTIFUNGAL ACTIVITIES
OKI, T
HIRANO, M
TOMATSU, K
NUMATA, KI
KAMEI, H
[J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (12) : 1756 - 1762
[19] DIRECT H-1-NMR ASSAY OF THE ENANTIOMERIC COMPOSITION OF AMINES AND BETA-AMINO ALCOHOLS USING O-ACETYL MANDELIC-ACID AS A CHIRAL SOLVATING AGENT
PARKER, D
TAYLOR, RJ
[J]. TETRAHEDRON, 1987, 43 (22) : 5451 - 5456
[20] NEW SYNTHETIC REACTIONS - SULFENYLATIONS AND DEHYDROSULFENYLATIONS OF ESTERS AND KETONES
TROST, BM
SALZMANN, TN
HIROI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (16) : 4887 - 4902

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