Total Synthesis of Daphniphyllum Alkaloids: (+)-Daphlongamine E, (+)-Calyciphylline R, and (–)-10-Deoxydaphnipaxianine A

Yan Zhang; Yuye Chen; Jing Xu

doi:10.1055/a-2244-1600

Synthesis, Table of Contents

Synthesis 2024; 56(08): 1273-1284
DOI: 10.1055/a-2244-1600

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New Trends in Organic Synthesis from Chinese Chemists

Total Synthesis of Daphniphyllum Alkaloids: (+)-Daphlongamine E, (+)-Calyciphylline R, and (–)-10-Deoxydaphnipaxianine A

Yan Zhang‡

,

Yuye Chen‡

,

Jing Xu ∗

Abstract

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Abstract

Here, we wish to describe our detailed efforts in the total synthesis of three calyciphylline A-type alkaloids, namely (+)-daphlongamine E, (+)-calyciphylline R, and (–)-10-deoxydaphnipaxianine A. Important steps in our approach include a Pt-catalyzed nitrile hydration, a Babler–Dauben rearrangement, a novel selective amide reduction tactic, and an oxidative Nazarov cyclization via an unfunctionalized tertiary divinyl carbinol (TDC).

Key words

Daphniphyllum alkaloids - total synthesis - oxidative Nazarov cyclization - Babler–Dauben rearrangement - amide reduction - nitrile hydration

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References

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