Bufadienolidies. 4. Reaction of 20-oxo steroids with methoxymethylenetriphenylphosphorane

George Pettit, Brian Green, George L. Dunn, Paul Sunder-Plassmann

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Reaction of 20-oxo-5-pregnenes 1a-1c with the ylide prepared from methoxymethyltriphenylphosphonium chloride was studied in detail. Vinyl ether 2a was also obtained along with a comparable amount of 3β-acetoxy-26,27-bisnor-5,20(22)cholestadiene (3a), employing the mixture of phosphoranes from methoxymethyltri-n-butylphosphonium chloride. Acid-catalyzed hydrolysis of vinyl ether 2 afforded aldehyde 4. Attempts to condense methoxymethylenetriphenylphosphorane with trans olefinic ketono 5a, cis olefinic ketone 6a, or saturated ketone 7a led to extensive side reactions attributable to the methyl ester group. Use of the carboxylic acid (7j) or the t-butyl ester (7b) or amide (7d) eliminated side reactions but satisfactory involvement of the 20 ketone was not realized.

Original languageEnglish (US)
Pages (from-to)1385-1389
Number of pages5
JournalJournal of Organic Chemistry
Volume35
Issue number5
StatePublished - 1970

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Ketones
Steroids
Cholestadienes
Chlorides
Esters
Phosphoranes
Pregnenes
Carboxylic Acids
Aldehydes
Amides
Hydrolysis
Acids
vinyl ether

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bufadienolidies. 4. Reaction of 20-oxo steroids with methoxymethylenetriphenylphosphorane. / Pettit, George; Green, Brian; Dunn, George L.; Sunder-Plassmann, Paul.

In: Journal of Organic Chemistry, Vol. 35, No. 5, 1970, p. 1385-1389.

Research output: Contribution to journalArticle

Pettit, G, Green, B, Dunn, GL & Sunder-Plassmann, P 1970, 'Bufadienolidies. 4. Reaction of 20-oxo steroids with methoxymethylenetriphenylphosphorane', Journal of Organic Chemistry, vol. 35, no. 5, pp. 1385-1389.
Pettit, George ; Green, Brian ; Dunn, George L. ; Sunder-Plassmann, Paul. / Bufadienolidies. 4. Reaction of 20-oxo steroids with methoxymethylenetriphenylphosphorane. In: Journal of Organic Chemistry. 1970 ; Vol. 35, No. 5. pp. 1385-1389.
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