Cyano diallylamine additions to glycoside and nucleoside aldehydes and itsapplication to the synthesis of polyoxin L and uracil polyoxin C

Citation
Kmk. Kutterer et G. Just, Cyano diallylamine additions to glycoside and nucleoside aldehydes and itsapplication to the synthesis of polyoxin L and uracil polyoxin C, HETEROCYCLE, 51(6), 1999, pp. 1409
Citations number
45
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
51
Issue
6
Year of publication
1999
Database
ISI
SICI code
0385-5414(19990601)51:6<1409:CDATGA>2.0.ZU;2-6
Abstract
Three efficient, high yielding syntheses of precursors (1) of carbamoylpoly oxamic acid from L-arabinose, based on the simultaneous addition of the aci d and amine functionalities, are described. Utilizing the same methodology and uridine as the starting material, an expedient 3 step (61% overall yiel d) synthesis of protected uracil polyoxin C (or the nucleoside moiety of po lyoxin L, 2), is also described.