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Published on: June 13, 2022
α,β-Epoxy Ketone Rearrangements for the Practical Synthesis of Cephalotaxine and the Stereodivergent Synthesis of
Cui-Cui Wang1, Huai-Yuan Yang1, Chang Liu1
1College of Chemical & Pharmaceutical Engineering, Hebei Province Key Laboratory of Molecular Chemistry for Drug, Hebei University of Science & Technology, Shijiazhuang 050018, China.
Abstract:
We report herein that three facile rearrangements of epoxy ketones can be employed for the efficient and practical synthesis of cephalotaxine, the parent member of the family of Cephalotaxus alkaloids. The Meinwald rearrangement of epoxy ketone (90%) was used for the preparation of the dense functional groups in the cyclopentane ring of cephalotaxine. A novel acid-catalyzed umpolung SN2' rearrangement and the Wharton transposition reaction of epoxy ketones were also developed to synthesize the Mori intermediate via the key azaspiro allylic alcohols in a stereodivergent manner.
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