Helvetica Chimica Acta p. 1527 - 1540 (1994)
Update date:2022-07-30
Topics:
Lang
Moser
The present work describes a new and efficient method for the preparation of either racemic or enantiomerically pure carbocyclic 2'-deoxyribonucleosides 1. Key steps are the efficient assembly of the racemic carbocyclic 2'-deoxyribose core (±)-12, its enzymatic resolution, and a new approach to covalently link the purine and pyrimidine bases with the cyclopentane moiety via the cyclic sulfate (+)-19. This total synthesis of enantiomerically pure and racemic carbocyclic 2'-deoxyribonucleosides 1 represents one of the most efficient approaches reported to date. Starting from cyclopentadiene, the four carbocycles corresponding to the naturally occurring 2'-deoxyribonucleosides could be prepared in 12 steps and 9-12% overall yield. For the corresponding racemic compounds, 10 steps were used with overall yields between 22 and 30%.
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Doi:10.1002/hlca.19480310247
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(1994)Doi:10.1021/jo991714z
(2000)Doi:10.1007/BF00777134
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(2014)Doi:10.1002/ejoc.201701245
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