PDF herunterladen
Synthesis 1993; 1993(4): 411-420
DOI: 10.1055/s-1993-25874
paper
© 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.

A Concise, Efficient and Flexible Strategy for the Synthesis of the Pheromones of Oryzaephilus and Cryptolestes Grain Beetles

Christopher D. J. Boden* , John Chambers, Ian D. R. Stevens
  • *Department of Chemistry, The University, Highfield, Southampton SO9 5NH, England
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
17. September 2002 (online)

 als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Six of the seven macrolide components of the pheromone systems of grain beetles of the genera Oryzaephilus and Cryptolestes are synthesised by new routes of greatly improved efficiency. Iterative methodology based on the Wittig olefination is employed for the construction of the (Z,Z)-1,4-diene subunits in three of the lactones; chlorite oxidation of (Z)-3-alkenals derived by this methodology is used to form the (Z)-3-alkenoic acid functionalities present in four of the targets. The use of recently described conditions for the cyclisation of a Combretastatin analogue gives dramatically increased yields for the macrolactonisation steps in all six cases.