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

(opens in new window) Buy Article (opens in new window) Permissions and Reprints (opens in new window) All articles of this category (opens in new window) 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