PDF herunterladen
Synlett 1996; 1996(12): 1221-1223
DOI: 10.1055/s-1996-5707
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of Spiro[4.5]decan-1-ones: A Formal Synthesis of Acoradienes and Related Sesquiterpenes via Rhodium-catalyzed Claisen Rearrangement/Hydroacylation

Tim Sattelkau, Christoph Hollmann, Peter Eilbracht*
  • *Organische Chemie I (FB 3), Universität Dortmund, Otto-Hahn-Str. 6, D-44227 Dortmund, Germany, Fax: (+49) (0)231/7555363, e-mail: eilbrach@citrin.chemie.uni-dortmund.de
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

A novel procedure for the synthesis of spiro[4.5]decan-1-ones starting from commercially available substances is described. The key-step is a one-pot combination of Claisen rearrangement of allyl vinyl ethers followed by an intramolecular hydroacylation1 catalysed by RhCl(cod)(dppe).2 The intermediate pent-4-enals generated by the initial [3.3] sigmatropic rearrangement exhibit substitution patterns which have previously been described as unsuitable for the rhodium catalysed intramolecular hydroacylation.3,4 This procedure allows the synthesis of ketone 2, a key intermediate in the total synthesis of acoradienes and acorones.5

acoradienes - spirocyclopentannulation - Claisen rearrangement - hydroacylation - transition metal catalysis