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

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 ins

SUBMITTER: Chen W 

PROVIDER: S-EPMC8854706 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature