Issue 11, 1970

A synthesis of the insect moulting hormone, ecdysone, and related compounds

Abstract

A relatively short synthesis of the insect moulting hormone, ecdysone, and of its C-22 isomer is described, starting from ergosterol. A key step is the direct transformation of the 3α,5α-cycloergosta-7,22-dien-6-one (5) into the 14α- and 14β-ergosta-2,7,22-trien-6-ones (11 and 12). Selective cis-hydroxylation of the 2-enes, followed by enol acetylation and oxidation with perphthalic acid afforded the 5α-ecdysone nucleus. Ozonolysis of the C-22 double bond gave (20S)-2β,3β-diacetoxy-20-formyl-14α-hydroxy-5α-pregn-7-en-6-one, to which the ecdysone side chain was attached in a known manner.

Article information

Article type
Paper

J. Chem. Soc. C, 1970, 1584-1591

A synthesis of the insect moulting hormone, ecdysone, and related compounds

D. H. R. Barton, P. G. Feakins, J. P. Poyser and P. G. Sammes, J. Chem. Soc. C, 1970, 1584 DOI: 10.1039/J39700001584

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