Synthesis of highly functionalized cyclodecenone derivatives from siloxycyclopropanes: Scope and limitations

[摘要]：Alkenyl substituted 2-siloxycyclopropanecarboxylates 1a-c were converted into chain elongated compounds 2a-m by a highly flexible two step sequence. Precursors 2a-m underwent fluoride promoted desilylation, ring cleavage and (in most cases) intramolecular Michael addition furnishing cyclodecenone derivatives 3. The success of this one-pot procedure depends on the kind of pronucleophilic unit and the substitution pattern of the double bond to be attacked. Furthermore, the connecting spacer also influenced the outcome of the reaction. Despite of some limitations this straightforward method allows constructions of a variety of cyclodecenone derivatives.

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