Steroids and Related Natural Products. VI. The Structure of α-Apoallobetulin

George R. Pettit, Brian Green, William J. Bowyer

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Abstract

The allobetulin dehydration product, α-apoallobetulin, has been shown to be represented by structure IV. Initial support for this assignment was obtained by oxidizing α-apoallobetulin to a diketone (VII). Direct oxidation of α-apoallobetulin to diketone VII was unexpectedly achieved employing a modified osmium tetroxide-pyridine procedure. The same oxidation product was prepared by ozonization of α-apoallobetulin and by lead tetraacetate oxidation of its glycol derivative (VI). Substantial evidence favoring the proposed endocvclic olefin (IV) formulation was provided by the facile isomerization of δ-apoallobetulin (III) to α-apoallobetulin. The ketone (VIII) obtained following ozonization of δ-aponllohetulin was assigned an A/B cis-configuration on the basis of optical rotatory dispersion measurements.

Original languageEnglish (US)
Pages (from-to)2879-2883
Number of pages5
JournalJournal of Organic Chemistry
Volume26
Issue number8
DOIs
StatePublished - Aug 1961
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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