Programmable meroterpene synthesis

Xingyu Shen, Chi P. Ting, Gong Xu and Thomas J. Maimone ()
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Xingyu Shen: University of California, Berkeley
Chi P. Ting: University of California, Berkeley
Gong Xu: University of California, Berkeley
Thomas J. Maimone: University of California, Berkeley

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract 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.

Date: 2020
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DOI: 10.1038/s41467-020-14354-5

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