Steroids and related natural products. VI. The structure of α-apoallobetulin

George Pettit, Brian Green, William J. Bowyer

Research output: Contribution to journalArticle

21 Citations (Scopus)

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 endocyclic olefin (IV) formulation was provided by the facile isomerization of δ-apoallobetulin (III) to α-apoallobetulin. The ketone (VIII) obtained following ozonization of δ-apoallobetulin 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
StatePublished - 1961
Externally publishedYes

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Biological Products
Ozonization
Steroids
Oxidation
Osmium Tetroxide
Glycols
Alkenes
Isomerization
Ketones
Dehydration
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Steroids and related natural products. VI. The structure of α-apoallobetulin. / Pettit, George; Green, Brian; Bowyer, William J.

In: Journal of Organic Chemistry, Vol. 26, No. 8, 1961, p. 2879-2883.

Research output: Contribution to journalArticle

Pettit, George ; Green, Brian ; Bowyer, William J. / Steroids and related natural products. VI. The structure of α-apoallobetulin. In: Journal of Organic Chemistry. 1961 ; Vol. 26, No. 8. pp. 2879-2883.
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