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Research article1995Peer reviewed

The diastereospecific synthesis of new 2′,3′-Cis-α-fused carbocyclic nucleosides

Papchikhin, A.; Agback, P.; Plavec, J.; Chattopadhyaya, J.

Abstract

The first diastereospecific synthesis of [3.3.0]- and [3.4.0]-alpha-cis-fused-carbocyclic nucleosides 10, 12 and 20, starting directly from 2'-O-(TBDMS) or 3'-O-(TBDMS) derivatives of 5'-O-MMTr-2',3'-seco-ribo-thymidines, 1 and 13 (ref. 4), have been reported. The key steps involve the unsymmetrical modification of the 2'- and 3'-hydroxyls in seco-nucleosides 1 and 13 and their diastereospecific recyclisalion to the furanose-fused carbocyclic rings using either radical cyclization [1-->2-->3(72%)-->4(90%)-->5(83%)-->6-->7(77%)-->8(61%)-->(41%) and 11(42%);9-->10 (87%) and 11-->12(84%)] or Diels-Alder reaction [13-->14-->15(91%)-->16(80%)-->17-->18(36%)-->19(69%)-->20(84%)].

Published in

Tetrahedron
1995, volume: 51, number: 1, pages: 329-342
Publisher: PERGAMON-ELSEVIER SCIENCE LTD

SLU Authors

UKÄ Subject classification

Organic Chemistry

Publication identifier

  • DOI: https://doi.org/10.1016/0040-4020(94)00950-Y

Permanent link to this page (URI)

https://res.slu.se/id/publ/83899