SYNTHESIS OF HIGHLY FUNCTIONALIZED CYCLODECENONE DERIVATIVES FROM SILOXYCYCLOPROPANES - SCOPE AND LIMITATIONS

Alkenyl substituted 2-siloxycyclopropanecarboxylates 1a-c were convert ed into chain elongated compounds 2a-m by a highly flexible two step s equence. Precursors 2a-m underwent fluoride promoted desilylation, rin g cleavage and (in most cases) intramolecular Michael addition furnish ing cyclodecenone derivatives 3. The success of this one-pot procedure depends on the kind of pronucleophilic unit and the substitution patt ern of the double bond to be attacked. Furthermore, the connecting spa cer also influenced the outcome of the reaction. Despite of some limit ations this straightforward method allows constructions of a variety o f cyclodecenone derivatives.