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

Three efficient, high yielding syntheses of precursors (1) of carbamoylpolyoxamic acid from L-arabinose, based on the simultaneous addition of the acid and amine functionalities, are described. Utilizing the same methodology and uridine as the starting material, an expedient 3 step (61% overall yiel...

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Bibliographic Details
Published inHeterocycles Vol. 51; no. 6; pp. 1409 - 1421
Main Authors Kutterer, KMK, Just, G
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.06.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
4-O-BENZYL-2,3-O-ISOPROPYLIDENE-L-THREOSE
(+)-POLYOXIN-J
PROTECTING GROUP
PENALDIC ACID EQUIVALENT
5-O-CARBAMOYLPOLYOXAMIC ACID
AMINO-ACIDS
(1-ETHOXYVINYL)LITHIUM
STEREOCONTROLLED BUILDUP
CHITIN SYNTHETASE
STEREOSELECTIVE SYNTHESIS
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Summary:Three efficient, high yielding syntheses of precursors (1) of carbamoylpolyoxamic acid from L-arabinose, based on the simultaneous addition of the acid and amine functionalities, are described. Utilizing the same methodology and uridine as the starting material, an expedient 3 step (61% overall yield) synthesis of protected uracil polyoxin C (or the nucleoside moiety of polyoxin L, 2), is also described.
ISSN:0385-5414
DOI:10.3987/com-99-8520