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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Forging the Tetracyclic Core Framework of Rhodomolleins XIV and XLII: A Ring-Distortion Approach
Zhen-Ning Yang1, Huijuanzi Rao1, Yuhao Yin1
1Department of Chemistry, Zhejiang University, Hangzhou 310058, China.
Abstract:
A ring distortion approach for the synthesis of an advanced intermediate en route to rhodomolleins XIV and XLII was described, which led to successful construction of the 5/8/5/5 tetracyclic core framework of the kalmane diterpenoids. Key steps of the strategy include an oxidative dearomatization-induced (ODI)-Diels-Alder cycloaddition, a Dowd-Beckwith rearrangement, and a bioinspired Wagner-Meerwein rearrangement.
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