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

New Alkaloids of the ent-Kaurene Type From Anopterus Species (Escalloniaceae). I. The Structure and Reactions of Anopterine

N Hart, S Johns, J Lamberton, H Suares and R Willing

Australian Journal of Chemistry 29(6) 1295 - 1318
Published: 1976

Abstract

Anopterine (1), a major alkaloid from leaf and bark of Anoptevus macleayanus F. Muell. and bark of Anoptevus glandulosus Labill., has an unusual ent-kaurenoid skeleton with a C20-C14 linkage. Hydrolysis of anopterine gives anopteryl alcohol (5), C21H31N05, and two equivalents of tiglic acid. The chemical reactions of anopterine and anopteryl alcohol have been studied in detail, and a number of acetylation products and oxidation products have been obtained. Oxidation of anopteryl alcohol with potassium ferricyanide has given an unusual product (14) which has a C20,C12-oxide bridge and a C5,C6-epoxide group.

https://doi.org/10.1071/CH9761295

© CSIRO 1976

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