Terpenoids. Part XVIII. A common stereoelectronic requirement in epimerisations and retro-Dieckmann-type cleavages of some diterpene alcohols and ketones
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 2902-2907
- https://doi.org/10.1039/j39710002902
Abstract
A stereoelectronic factor controlling epimerisations of the C-15 alcohols (2)—(5) derived from enmein (1)(which have a cis-relationship between the 15-hydroxy- and 16-methyl groups) into the corresponding trans-alcohols (6)—(9) also operates in the retro-Dieckmann-type cleavage of the related C-15 ketones (30) and (10) to give the carboxylic acids (31) and (33). The mechanism of these reactions is discussed.Keywords
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