A STEREOSELECTIVE AND EFFICIENT ROUTE TO (3S,4R,5S)-(-4,5-DIHYDROXYCYCLOPENT-1-EN-3-YLAMINE - THE SIDE-CHAIN OF THE HYPERMODIFIED NUCLEOSIDE-Q())

Authors
OVAA H CODEE JDC LASTDRAGER B OVERKLEEFT HS VANDERMAREL GA VANBOOM JH
Citation
H. Ovaa et al., A STEREOSELECTIVE AND EFFICIENT ROUTE TO (3S,4R,5S)-(-4,5-DIHYDROXYCYCLOPENT-1-EN-3-YLAMINE - THE SIDE-CHAIN OF THE HYPERMODIFIED NUCLEOSIDE-Q()), Tetrahedron letters, 39(43), 1998, pp. 7987-7990
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
43
Year of publication
1998
Pages
7987 - 7990
Database
ISI
SICI code
0040-4039(1998)39:43<7987:ASAERT>2.0.ZU;2-N
Abstract
A stereoselective and high yielding route is described to a suitably p rotected derivative of (3S, 4R, 5S)-(+)-3-amino-4,5-dihydroxycyclopent -1-ene, the side chain moiety of queuosine. The synthetic route compri ses a ring-closing metathesis (RCM) of a mannofuranose-derived diene f ollowed by Overman rearrangement. (C) 1998 Elsevier Science Ltd. All r ights reserved.