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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Dihydropyrrolizines. III. Preparation and reactions of derivatives related to pyrrolizidine alkaloids

CCJ Culvenor, JA Edgar, LW Smith and HJ Tweeddale

Australian Journal of Chemistry 23(9) 1853 - 1867
Published: 1970

Abstract

1,2-Dehydropyrrolizidine derivatives, mainly the hepatotoxic alkaloids and their amino alcohols, are converted into 6,7-dihydro-5H-pyrrolizine derivatives. The dehydro derivatives of the amino alcohols are prepared with chloranil. Oxidation by manganese dioxide or potassium permanganate, or catalytic dehydrogenation, also leads to the desired dihydropyrrolizines together with products at a higher oxidation level such as 7-oxo and 1-formyl derivatives. The dehydro derivatives of the ester alkaloids are best prepared by the action of acetic anhydride on the N-oxides. The reactions of the dihydropyrrolizines with alcohols and amines, and their N.M.R. spectra, are discussed.

https://doi.org/10.1071/CH9701853

© CSIRO 1970

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