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Abstract: (Chemical Abstract 2000, 133:238147)
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Maslinic acid was obtained from olive-pressing residues, and several derivatives were formed.
Rearrangements of 2-tosyloxy-derivatives of methyl maslinate made out by acetolysis.
The main product of these rearrangements contained a cyclopentanic A-ring as a result
of a concerted 2(3)-> 4-abeo rearrangement process. Moreover, when there was a ketone
group at C-3 in the tosyloxy derivative, this concerted rearrangement did not occur,
and only cyclohexanic compounds were formed. Experimental 13C NMR
chemical shifts are
given and a comparison with the theoretical 13C shifts
(GIAO method with the MM+
geometries at the B3LYP/6-31G* level) showed good agreement between the two values.
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