Abstract
A concise and stereoselective synthesis of a CDE-seco limonoid related to ohchinolide
and nimbolidin was accomplished in eleven and twelve steps, respectively,
from α-cyclocitral. Opening of the C ring was first attempted
by a retro-Claisen reaction, whereby a very unusual rearrangement
occurred. However, the ring-opening was successfully accomplished
by a selective Baeyer-Villiger reaction.
Key words
stereoselective synthesis - allylic rearrangement - C-seco limonoids - ohchinolide - nimbolidin
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7 Crystallographic data (excluding structure
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[10
10 All compounds synthesised are racemic
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13 Essays of insect antifeedant activity
of all compounds described in this work will be published in due
course.
