Addition of lithiated 9-deazapurine derivatives to a carbohydrate cyclic imine: convergent synthesis of the aza-C-nucleoside immucillins

G B Evans; R H Furneaux; T L Hutchison; H S Kezar; P E Morris Jr; V L Schramm; P C Tyler

doi:10.1021/jo0155613

Addition of lithiated 9-deazapurine derivatives to a carbohydrate cyclic imine: convergent synthesis of the aza-C-nucleoside immucillins

J Org Chem. 2001 Aug 24;66(17):5723-30. doi: 10.1021/jo0155613.

Authors

G B Evans¹, R H Furneaux, T L Hutchison, H S Kezar, P E Morris Jr, V L Schramm, P C Tyler

Affiliation

¹ Carbohydrate Chemistry, Industrial Research Limited, P.O. Box 31310, Lower Hutt, New Zealand.

PMID: 11511245
DOI: 10.1021/jo0155613

Abstract

Means have been developed for the synthesis and addition of 9-deaza-9-lithiopurine derivatives to the carbohydrate-derived cyclic imine 6 in facile convergent syntheses of biologically active aza-C-nucleosides.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Imines / chemistry*
Lithium / chemistry*
Purines / chemistry*
Pyrimidine Nucleosides / chemical synthesis*
Pyrimidinones / chemical synthesis*
Pyrroles / chemical synthesis*

Substances

Imines
Purines
Pyrimidine Nucleosides
Pyrimidinones
Pyrroles
Lithium