Carbohydrate-based synthesis of crocacin: stereoselective Heck reaction of carbohydrate 5,6-ene- and 5,6-yne-derivatives with aromatic halides

被引：18

作者：

Gurjar, MK ^{[1
]}

Khaladkar, TP ^{[1
]}

Borhade, RG ^{[1
]}

Murugan, A ^{[1
]}

机构：

[1] Natl Chem Lab, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(03)01256-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Heck reaction between a carbohydrate 5,6-ene derivative 9 and an aromatic halide exclusively gave rise to the beta-carbohydrate-substituted trans-styrene derivative 8; while the corresponding Wittig reaction produced a cis/trans mixture in which the cis-isomer predominated. The application of the Heck reaction is described to synthesize the intermediate 5, commonly used in the synthesis of members of the crocacin family. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：5183 / 5187

页数：5

相关论文

共 20 条

[1] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[2] SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITIES IN CATALYZED AND UNCATALYZED HYDROBORATIONS OF ACYCLIC ALLYLIC ALCOHOL DERIVATIVES - SECONDARY ORBITAL EFFECTS INVOLVING D-PI-P-PI INTERACTIONS [J].

BURGESS, K ;

CASSIDY, J ;

OHLMEYER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1020-1027

[3] ON CATALYZED AND UNCATALYZED HYDROBORATIONS OF CHIRAL ALLYLIC ALCOHOLS AND AMINES [J].

BURGESS, K ;

OHLMEYER, MJ .

TETRAHEDRON LETTERS, 1989, 30 (43) :5861-5864

[4] TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS [J].

BURGESS, K ;

OHLMEYER, MJ .

CHEMICAL REVIEWS, 1991, 91 (06) :1179-1191

[5] Total synthesis of (+)-crocacin C [J].

Chakraborty, TK ;

Jayaprakash, S ;

Laxman, P .

TETRAHEDRON, 2001, 57 (46) :9461-9467

[6]

Chakraborty TK, 2001, TETRAHEDRON LETT, V42, P497, DOI 10.1016/S0040-4039(00)02002-5

[7]

Crisp GT, 1998, CHEM SOC REV, V27, P427

[8] Total synthesis of (+)-crocacin C [J].

Dias, LC ;

de Oliveira, LG .

ORGANIC LETTERS, 2001, 3 (24) :3951-3954

[9] RHODIUM(I)-CATALYZED HYDROBORATION OF OLEFINS - THE DOCUMENTATION OF REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN CYCLIC AND ACYCLIC SYSTEMS [J].

EVANS, DA ;

FU, GC ;

HOVEYDA, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6917-6918

[10] Total synthesis of (+)-crocacin D [J].

Feutrill, JT ;

Lilly, MJ ;

Rizzacasa, MA .

ORGANIC LETTERS, 2002, 4 (04) :525-527