CONCISE RACEMIC AND HIGHLY ENANTIOSELECTIVE APPROACHES TO KEY INTERMEDIATES FOR THE SYNTHESES OF CARBOCYCLIC NUCLEOSIDES AND PSEUDO-RIBOFURANOSES - FORMAL SYNTHESES OF CARBOVIR

被引:68
作者
HODGSON, DM [1 ]
WITHERINGTON, J [1 ]
MOLONEY, BA [1 ]
机构
[1] AGREVO UK LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 23期
关键词
D O I
10.1039/p19940003373
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A regio- and stereo-specific synthesis of cis-(+/-)-3-acetoxy-5-(acetoxymethyl)cyclopentene 3 from cyclopent-3-enecarboxylic acid 4 via a bromolactonisation strategy is described. Pd-catalysed coupling of the cis-(+/-)-diacetate 3 with 2-amino-6-chloropurine or 2.6-diaminopurine leads to the formal syntheses of carbovir 1. A synthesis of the (1R) cis-diacetate 15 (R = Ac) is described via a highly enantioselective rearrangement of cis-6-oxabicyclo[3.1.0] hexane-3-methanol 13 (also prepared from the acid 4) using the dilithium salt of (1S,2R) norephedrine.
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页码:3373 / 3378
页数:6
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