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.
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