Pericyclization of Vinylallenes in Organic Synthesis: On the Intramolecular Diels-Alder Reaction
- 1 January 1990
- journal article
- account
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (01) , 1-9
- https://doi.org/10.1055/s-1990-20973
Abstract
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. SummaryKeywords
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