Keywords
allyl bromide
cyrene
ginkgolides
intramolecular cationic cyclization
trichothecene sesquiterpenoids
Abstract
The reaction of cyrene with allyl bromide in THF in the presence of ButOK gave the α,α-diallyl derivative of cyrene in 50% yield. This derivative smoothly undergoes iodo- cyclization on the keto group that is converted into a ketal center to give annulated bis-tetrahydrofuran; intramolecular cationic cyclization in the presence of SnCl4 or TiCl4 results in 2-oxabicyclo[3.3.1]nonan-9-ones. The prospects of using these reactions towards the synthesis of trichothecene sesquiterpenoids modified in the central moiety were assessed.
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