PDF icon PDF herunterladen
Synlett 1990; 1990(1): 1-9
DOI: 10.1055/s-1990-20973
account
© 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.

Pericyclization of Vinylallenes in Organic Synthesis: On the Intramolecular Diels-Alder Reaction

William H. Okamura* , Michael L. Curtin
  • *Department of Chemistry, University of California, Riverside, Riverside, CA 92521, USA
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
08. März 2002 (online)

 als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

A scheme for the classification of the intramolecular Diels-Alder (IMDA) reaction of vinylallenes utilized as the diene component in the process is suggested. One variant of this process, wherein the dienophile is tethered to the allenic terminus of a cycloalkenylallene, has been explored in terms of its scope and reactivity as well as exemplified by its application in the highly stereoselective syntheses of a variety of linearly fused polycycles and the natural product (+)-sterpurene. 1. Introduction 1.1. Vinylallenes 1.2. Classification of Cyclizations 2. Studies of the Type I IMDA Reaction with Cycloalkenylallenes 2.1. Scope and Reactivity Studies 2.2. Application Studies: (+)-Sterpurene 3. Summary