Structure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids.
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
17 02 2022
17 02 2022
Historique:
received:
21
06
2021
accepted:
21
01
2022
entrez:
18
2
2022
pubmed:
19
2
2022
medline:
4
3
2022
Statut:
epublish
Résumé
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 SmI
Identifiants
pubmed: 35177620
doi: 10.1038/s41467-022-28535-x
pii: 10.1038/s41467-022-28535-x
pmc: PMC8854706
doi:
Substances chimiques
Indole Alkaloids
0
koumine
0
Ajmaline
1PON08459R
sarpagine
XD54MPV6VQ
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
908Informations de copyright
© 2022. The Author(s).
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