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Title: Programmable meroterpene synthesis Nat Commun 11, 508 (2020). https://doi.org/10.1038/s41467-020-14354-5
The bicyclo[3.3.1]nonane architecture is a privileged structural motif found in over 1000 natural products with relevance to neurodegenerative disease, bacterial and parasitic infection, and cancer among others. Despite disparate biosynthetic machinery, alkaloid, terpene, and polyketide-producing organisms have all evolved pathways to incorporate this carbocyclic ring system. Natural products of mixed polyketide/terpenoid origins (meroterpenes) are a particularly rich and important source of biologically active bicyclo[3.3.1]nonane-containing molecules. Herein we detail a fully synthetic strategy toward this broad family of targets based on an abiotic annulation/rearrangement strategy resulting in a 10-step total synthesis of garsubellin A, an enhancer of choline acetyltransferase and member of the large family of polycyclic polyprenylated acylphloroglucinols. This work solidifies a strategy for making multiple, diverse meroterpene chemotypes in a programmable assembly process involving a minimal number of chemical transformations.
Authors:
; ; ;
Award ID(s):
1554544
Publication Date:
NSF-PAR ID:
10141032
Journal Name:
Nature communications
Volume:
11
Issue:
508
Page Range or eLocation-ID:
1-8
ISSN:
2041-1723
Sponsoring Org:
National Science Foundation
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