A SIMPLE AND HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF A 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE BY DEALLYLOXYCARBONYLATION USING PALLADIUM COMPLEXES

被引：26

作者：

MURAYAMA, T ^{[1
]}

YOSHIDA, A ^{[1
]}

KOBAYASHI, T ^{[1
]}

MIURA, T ^{[1
]}

机构：

[1] TAKASAGO INT CORP,CENT RES LAB,HIRATSUKA 254,KANAGAWA,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 15期

关键词：

D O I：

10.1016/0040-4039(94)85196-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Simple, highly diastereoselective synthesis of the key 1 beta-methylcarbapenem intermediate 1 has been accomplished via a palladium catalyzed deallyloxycarbonylation of diallyl malonate derivative 4a which was readily prepared from (3S,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidimone 2 in two steps.

引用

页码：2271 / 2274

页数：4

共 50 条

[41] SYNTHETIC STUDIES OF CARBAPENEM AND PENEM ANTIBIOTICS .5. EFFICIENT SYNTHESIS OF THE 1-BETA-METHYLCARBAPENEM SKELETON [J].

SUNAGAWA, M ;

SASAKI, A ;

MATSUMURA, H ;

GODA, K ;

TAMOTO, K .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (07) :1381-1387

[42] CHEMISTRY OF O-SILYLATED KETENE ACETALS - AN EFFICIENT SYNTHESIS OF CARBAPENEM AND 1-BETA-METHYLCARBAPENEM INTERMEDIATES [J].

KITA, Y ;

SHIBATA, N ;

TOHJO, T ;

YOSHIDA, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (14) :1795-1799

[43] A NOVEL SYNTHESIS OF THE 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE EMPLOYING THE [2+2]-CYCLOADDITION REACTION OF CHLOROSULFONYL ISOCYANATE WITH A 4H-1,3-DIOXIN DERIVATIVE [J].

ITO, Y ;

KOBAYASHI, Y ;

TERASHIMA, S .

TETRAHEDRON LETTERS, 1989, 30 (41) :5631-5634

[44] A practical and stereocontrolled synthesis of a versatile 1 beta-methylcarbapenem intermediate [J].

Oda, K ;

Yoshida, A .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1997, 45 (09) :1439-1446

[45] A SIMPLE AND HIGHLY STEREOSELECTIVE ROUTE TO A KEY INTERMEDIATE CARBOXYLIC-ACID FOR THE SYNTHESIS OF 1-BETA-METHYLCARBAPENEMS [J].

MORI, M ;

OIDA, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) :2389-2392

[46] SYNTHESIS OF 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATES INVOLVING THE LABILE ACYL AUXILIARY 4,4-DIMETHYL-1,3-OXAZOLIDINE-2-THIONE [J].

DEZIEL, R ;

FAVREAU, D .

TETRAHEDRON LETTERS, 1989, 30 (11) :1345-1348

[47] Synthesis of a chiral 1 beta-methylcarbapenem key intermediate using radical cyclization of N-vinylic alpha-bromo amides [J].

Ishibashi, H ;

Kameoka, C ;

Kodama, K ;

Kawanami, H ;

Hamada, M ;

Ikeda, M .

TETRAHEDRON, 1997, 53 (28) :9611-9622

[48] Highly stereoselective and practical synthesis of a key intermediate for 1-beta-methylcarbapenems [J].

Yamanaka, T ;

Seki, M ;

Kuroda, T ;

Ohmizu, H ;

Iwasaki, T .

TETRAHEDRON LETTERS, 1996, 37 (28) :4967-4968

[49] HYDROGENOLYSIS-ISOMERIZATION-REDUCTION OF PROPARGYL ACETATE, AND REGIOSELECTIVE AND STEREOSELECTIVE HYDROGENATION OF DIENYL ESTER FOR THE SYNTHESIS OF 1-BETA-METHYLCARBAPENEM PRECURSOR [J].

FUJISAWA, T ;

HAYAKAWA, R ;

SHIMIZU, M .

CHEMISTRY LETTERS, 1995, (11) :1013-1014

[50] A NEW SYNTHETIC ROUTE TO THE KEY PRECURSOR OF 1-BETA-METHYLCARBAPENEM ANTIBIOTICS FROM (S)-METHYL 3-HYDROXY-2-METHYLPROPANOATE [J].

SHIRAI, F ;

NAKAI, T .

CHEMISTRY LETTERS, 1989, (03) :445-448

← 1 2 3 4 5 →