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

Authors
Rhee, H Yoon, DO Jung, ME
Citation
H. Rhee et al., Efficient synthesis of carbocyclic nucleoside, (+/-)-homocarbovir via pi-allylpalladium complexes formation from the allyl N,N-ditosylimide substrate, NUCLEOS NUC, 19(3), 2000, pp. 619-628
Citations number
24
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
ISSN journal
15257770 → ACNP
Volume
19
Issue
3
Year of publication
2000
Pages
619 - 628
Database
ISI
SICI code
1525-7770(2000)19:3<619:ESOCN(>2.0.ZU;2-T
Abstract
The synthesis of a carbovir analogue, (+/-)-homocasbovir (3) was achieved f rom norbornadiene (4) in seven steps and 27% overall yield. This route invo lves a Meinwald-type rearrangement, an acid-hydrolysis of N-tosyl bicyclic enamine 5, and a Pd(0)-catalyzed coupling reaction.