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A Novel Sm(II)-Induced Route to Highly Substituted Benzannulated Cyclooctanol Derivatives
31 December 2000 (online)
Siloxycyclopropane derivatives 3 with a suitable styrene side chain can effectively be ring opened to precursors 2 which undergo reductive ring closure with SmI2 to furnish benzannulated cyclooctanols 1 or lactones 7 derived thereof. Tricyclic lactone 7c can be further substituted by conversion into a bridgehead enolate and reactions with electrophiles.
siloxycyclopropanes - samarium(II) iodide - Stille coupling - cyclooctanol - alkylation