Synthesis of 2,3-Benzobicyclo[3.3.1]non-2-enes via a Cascade of Domino Carbocation Migration/Interrupted Ritter Reaction and Dienone-Phenol Rearrangement
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引用次数: 0
Abstract
The 2,3-benzobicyclo[3.3.1]non-2-ene scaffold is a bridged backbone of many bioactive natural products. The development of a concise tactic toward this architecture is of keen interest and highly challenging. Herein, we disclose a novel cascade protocol for realizing this target. This approach relies on a domino sequence of carbocation rearrangement and Ritter reaction of the taiwaniaquinoid scaffold derivatives. A process of dienone-phenol rearrangement was postulated to be involved. Several potentially useful compounds with this intricate bridged ring were obtained in good overall yields (59–83%, over 2 steps).
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.