Structure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids

Wen Chen, Yonghui Ma, Wenyan He, Yinxia Wu, Yuancheng Huang, Yipeng Zhang, Hongchang Tian, Kai Wei, Xiaodong Yang () and Hongbin Zhang ()
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Wen Chen: Yunnan University
Yonghui Ma: Yunnan University
Wenyan He: Yunnan University
Yinxia Wu: Yunnan University
Yuancheng Huang: Yunnan University
Yipeng Zhang: Yunnan University
Hongchang Tian: Yunnan University
Kai Wei: Yunnan University
Xiaodong Yang: Yunnan University
Hongbin Zhang: Yunnan University

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: Abstract Sarpagine-Ajmaline-Koumine type monoterpenoid indole alkaloids represent a fascinating class of natural products with polycyclic and cage-like structures, interesting biological activities, and related biosynthetic origins. Herein we report a unified approach towards the asymmetric synthesis of these three types of alkaloids, leading to a collective synthesis of 14 natural alkaloids. Among them, akuammidine, 19-Z-akuammidine, vincamedine, vincarine, quebrachidine, vincamajine, alstiphylianine J, and dihydrokoumine are accomplished for the first time. Features of our synthesis are a new Mannich-type cyclization to construct the key indole-fused azabicyclo[3.3.1]nonane common intermediate, a SmI2 mediated coupling to fuse the aza-bridged E-ring, stereoselective olefinations to install either the 19-E or 19-Z terminal alkenes presented in the natural alkaloids, and an efficient iodo-induced cyclization to establish the two vicinal all-carbon quaternary centers in the Koumine-type alkaloids.

Date: 2022
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DOI: 10.1038/s41467-022-28535-x

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