Author:
Bell R. A.,Gravestock M. B.
Abstract
Low temperature ozonolysis of methyl podocarpate in methanol – methylene chloride results in the formation in high yield of 8β-hydroperoxy-8α-hydroxy-(13 → 17)-pentanorlabd-9(11)-en-12,19-dioic acid 19-methyl ester 8 → 12-lactone 4. Ozonolysis followed by hydrogen peroxide work-up gives the lactone-acid 14a, whilst ozonolysis followed by reduction with sodium borohydride gives keto-acid 3a and lactones 16 and 17 derived from peroxide 4 together with δ-lactone 19 possessing all 18 carbon atoms of methyl podocarpate. The lactone 16 is shown to possess an 8β-configuration by application of the nuclear Overhauser effect.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
27 articles.
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