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Synlett 1997; 1997(8): 995-997
DOI: 10.1055/s-1997-934
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A Novel Sm(II)-Induced Route to Highly Substituted Benzannulated Cyclooctanol Derivatives

Faiz Ahmed Khan, Regina Czerwonka, Reinhold Zimmer, Hans-Ulrich Reissig*
  • *Institut für Organische Chemie der Technischen Universität Dresden, D-01062 Dresden, Germany, Fax: +49 351 463 7030, E-mail: Hans.Reissig@chemie.tu-dresden.de
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Publikationsdatum:
31. Dezember 2000 (online)

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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