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Synthesis 2024; 56(08): 1273-1284
DOI: 10.1055/a-2244-1600
DOI: 10.1055/a-2244-1600
feature
New Trends in Organic Synthesis from Chinese Chemists
Total Synthesis of Daphniphyllum Alkaloids: (+)-Daphlongamine E, (+)-Calyciphylline R, and (–)-10-Deoxydaphnipaxianine A
Financial support from NSFC (No. 21971104 and 22271136), Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis (ZDSYS20190902093215877), Shenzhen Science, Technology and Innovation Commission (JCYJ20220814203252001), Guangdong Provincial Key Laboratory of Catalysis (No. 2020B121201002), Guangdong Innovative Program (No. 2019BT02Y335), Education Department of Guangdong Province, Key research projects in colleges and universities in Guangdong Province (2021ZDZX2035), Shenzhen Nobel Prize Scientists Laboratory Project (C17783101) and Innovative Team of Universities in Guangdong Province (2020KCXTD016) is greatly appreciated.
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 hydrationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2244-1600.
- Supporting Information
Publication History
Received: 12 December 2023
Accepted after revision: 12 January 2024
Accepted Manuscript online:
12 January 2024
Article published online:
13 February 2024
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