Literature DB >> 10843497

Efficient synthesis of carbocyclic nucleoside, (+/-)-homocarbovir via pi-allylpalladium complex formation from the allyl-N,N-ditosylimide substrate.

H Rhee1, D Yoon, M E Jung.   

Abstract

The synthesis of a carbovir analogue, (+/-)-homocarbovir (3) was achieved from norbornadiene (4) in seven steps and 27% overall yield. This route involves a Meinwald-type rearrangement, an acid-hydrolysis of N-tosyl bicyclic enamine 5, and a Pd(0)-catalyzed coupling reaction.

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Year:  2000        PMID： 10843497     DOI： 10.1080/15257770008035012

Source DB:  PubMed          Journal:  Nucleosides Nucleotides Nucleic Acids        ISSN： 1525-7770            Impact factor:   1.381


  3 in total

1.  Palladium-catalyzed decarboxylative rearrangements of allyl 2,2,2-trifluoroethyl malonates: direct access to homoallylic esters.

Authors:  Lawrence P Tardibono; Jerod Patzner; Cara Cesario; Marvin J Miller
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

2.  Ring expansion of substituted norbornadienes for the synthesis of mono- and disubstituted 2-azabicyclo[3.2.1]octadienes.

Authors:  Nova Emelda; Stephen C Bergmeier
Journal:  Tetrahedron Lett       Date:  2008-09-08       Impact factor: 2.415

3.  Enantioselective syntheses of carbocyclic nuleosides 5'-homocarbovir, epi-4'-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations.

Authors:  Lawrence P Tardibono; Marvin J Miller; Jan Balzarini
Journal:  Tetrahedron       Date:  2011-02-04       Impact factor: 2.457
  3 in total

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