CHEMISTRY OF O-SILYLATED KETENE ACETALS - A STEREOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE CARBAPENEM ANTIBIOTICS, (+)-THIENAMYCIN AND (+)-PS-5

被引：0

作者：

KITA, Y

SHIBATA, N

MIKI, T

TAKEMURA, Y

TAMURA, O

机构：

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1992年 / 40卷 / 01期

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D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A stereoselective synthesis of the chiral thienamycin intermediate (16) involving a diastereoselective Micheal addition and a silicon-induced Pummerer-type reaction is described. In a similar way, the key intermediate for (+)-PS-5 was also prepared from 4-(phenylsulfinylmethyl)butanamide (21).

引用

页码：12 / 20

页数：9

共 43 条

[21] CHEMISTRY OF O-SILYLATED KETENE ACETALS - A NOVEL INTRAMOLECULAR PUMMERER-TYPE REACTION OF OMEGA-CARBAMOYLSULFOXIDES LEADING TO ALPHA-THIOLACTAMS
KITA, Y
TAMURA, O
SHIBATA, N
MIKI, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (06) : 1473 - 1478
[22] CHELATION-CONTROLLED ENANTIOSELECTIVE SYNTHESIS OF KEY INTERMEDIATES FOR THE PREPARATION OF CARBAPENEM ANTIBIOTICS PS-5 AND 1-BETA-METHYL-PS-5
GENNARI, C
COZZI, PG
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17): : 4015 - 4021
[23] CHEMISTRY OF O-SILYLATED KETENE ACETALS - AN EFFICIENT SYNTHESIS OF ALPHA-THIO-N-HETEROCYCLES FROM OMEGA-AMIDOSULFOXIDES BY A NOVEL INTRAMOLECULAR PUMMERER-TYPE REARRANGEMENT
KITA, Y
TAMURA, O
MIKI, T
TAMURA, Y
TETRAHEDRON LETTERS, 1987, 28 (51) : 6479 - 6480
[24] SYNTHESIS OF OPTICALLY-ACTIVE (6R)-SUBSTITUTED (5R) CARBAPENEM
KOLLER, W
LINKIES, A
PIETSCH, H
REHLING, H
REUSCHLING, D
TETRAHEDRON LETTERS, 1982, 23 (15) : 1545 - 1548
[25] CHEMISTRY OF O-SILYLATED KETENE ACETALS - PREPARATION OF ALPHA-SILOXY PHENYL SULFIDES AND METHYL 3-(PHENYLTHIO)BUTYRATES FROM ALKYL PHENYL SULFOXIDES
KITA, Y
TAMURA, O
YASUDA, H
ITOH, F
TAMURA, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1985, 33 (10) : 4235 - 4241
[26] BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF THE TRANS-CARBAPENEM ANTIBIOTICS (+)-PS-5 AND (+)-PS-6
ANDREOLI, P
CAINELLI, G
PANUNZIO, M
BANDINI, E
MARTELLI, G
SPUNTA, G
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21): : 5984 - 5990
[27] SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY LACTONES BY SHARPLESS ASYMMETRIC DIHYDROXYLATIONS OF KETENE ACETALS, ENOL ETHERS, AND ENE LACTONES
CURRAN, DP
KO, SB
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21): : 6139 - 6141
[28] SYNTHETIC STUDIES ON CARBAPENEM ANTIBIOTICS FROM PENICILLINS .2. REGIOSELECTIVE AND STEREOSELECTIVE ALDOL REACTION OF A CHIRAL AZETIDINONE - A SYNTHESIS OF OPTICALLY-ACTIVE 6-EPICARPETIMYCINS
HIRAI, H
SAWADA, K
ARATANI, M
HASHIMOTO, M
TETRAHEDRON LETTERS, 1984, 25 (44) : 5075 - 5078
[29] SYNTHETIC STUDIES ON CARBAPENEM ANTIBIOTICS FROM PENICILLINS .3. STEREOSELECTIVE RADICAL REDUCTION OF A CHIRAL 3-ISOCYANOAZETIDINONE - A TOTAL SYNTHESIS OF OPTICALLY-ACTIVE CARPETIMYCINS
ARATANI, M
HIRAI, H
SAWADA, K
YAMADA, A
HASHIMOTO, M
TETRAHEDRON LETTERS, 1985, 26 (02) : 223 - 226
[30] HIGHLY DIASTEREOSELECTIVE ALDOL REACTIONS OF COBALT-COMPLEXED AND UNCOMPLEXED PROPYNALS WITH O-SILYL KETENE O,S-KETALS - HIGHLY STEREOSELECTIVE DIVERGENT FORMAL SYNTHESES OF THE BETA-LACTAM ANTIBIOTICS (+/-)-PS-5 AND (+/-)-EPI-PS-5
MUKAI, C
KATAOKA, O
HANAOKA, M
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (05): : 563 - 571

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