A new route to famciclovir via palladium catalysed allylation

Authors
Freer, R Geen, GR Ramsay, TW Share, AC Slater, GR Smith, NM
Citation
R. Freer et al., A new route to famciclovir via palladium catalysed allylation, TETRAHEDRON, 56(26), 2000, pp. 4589-4595
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
26
Year of publication
2000
Pages
4589 - 4595
Database
ISI
SICI code
0040-4020(20000623)56:26<4589:ANRTFV>2.0.ZU;2-P
Abstract
An efficient route to the acyclic nucleoside analogue famciclovir has been developed based on a palladium(0) catalysed coupling of 2-amino-6-chloropur ine and an allylic carbonate sidechain derived from 2,2-dimethyl-1,3-dioxan -5-one, The reaction proceeds via a highly N-9 regioselective purine allyla tion step involving a novel palladium mediated N-7 to N-9 rearrangement. (C ) 2000 Elsevier Science Ltd. All rights reserved.