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
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机构:
AGREVO UK LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLANDAGREVO UK LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND
HODGSON, DM
[1
]
WITHERINGTON, J
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AGREVO UK LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLANDAGREVO UK LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND
WITHERINGTON, J
[1
]
MOLONEY, BA
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AGREVO UK LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLANDAGREVO UK LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND
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.