The chemistry of castanospermine. Direct oxidation of the tetraacetate to the corresponding gamma-lactam

Richard H Furneaux; Graeme J Gainsford; Jennifer M Mason; Peter C Tyler

doi:10.1016/j.carres.2004.05.006

The chemistry of castanospermine. Direct oxidation of the tetraacetate to the corresponding gamma-lactam

Carbohydr Res. 2004 Jul 12;339(10):1747-51. doi: 10.1016/j.carres.2004.05.006.

Authors

Richard H Furneaux¹, Graeme J Gainsford, Jennifer M Mason, Peter C Tyler

Affiliation

¹ Industrial Research Ltd, PO Box 31-310, Lower Hutt, New Zealand.

PMID: 15220084
DOI: 10.1016/j.carres.2004.05.006

Abstract

From the products of oxidation of tetra-O-acetylcastanospermine (2) with N-bromosuccinimide, only the gamma-lactam 11 was isolated (19%). Treatment of this lactam with DBU in dichloromethane afforded the elimination product 12, while deacetylation with sodium methoxide in methanol gave tetraol 13 together with diene 14. The X-ray crystal structure of compound 13 is reported.

Publication types

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

MeSH terms

Acetates / chemistry*
Crystallography, X-Ray
Enzyme Inhibitors / pharmacology
Indolizines / chemistry*
Indolizines / isolation & purification
Lactams / chemistry*
Magnetic Resonance Spectroscopy
Methanol / chemistry
Methylene Chloride / chemistry
Models, Chemical
Models, Molecular
Oxidation-Reduction
Oxygen / chemistry*
Plant Proteins / chemistry
Seeds / metabolism
Spectrophotometry
X-Rays

Substances

Acetates
Enzyme Inhibitors
Indolizines
Lactams
Plant Proteins
Methylene Chloride
castanospermine
Oxygen
Methanol