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- Title
Steroids and Sexhormones. Part 265. Limonin, Part VI. Synthesis of a model compound incorporating rings D and E of 14,15-deepoxylimonin.
- Authors
Emmer, Gerhard; Graf, Walter
- Abstract
Starting from the known formyl ketene thioacetal 6, model compound 11 was synthesized. The key intermediates, the epimeric furylmethanols 7a and 7b, were converted into the same dithioortholactone 8b (Scheme 1) and further elaborated into the model compound 11 (Scheme 2), a versatile compound in the synthesis of limonin ( 1). The acid catalyzed conversion of the epimers 7a and 7b into 8b may probably involve a hydride-transfer reaction with inversion of configuration at C(17) of alcohol 7a ( Scheme 4, row b).
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 5, p1398
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640516