Annulative Methods Enable a Total Synthesis of the Complex Meroterpene Berkeleyone A

Synthetic pathways to complex meroterpenes derived from 3,5-dimethylorsellinic acid (DMOA) and farnesyl pyrophosphate have not been reported despite heavy biosynthetic and medicinal interest. Herein we report the first total synthesis of berkeleyone A, a potential gateway compound to a plethora of f...

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Published inJournal of the American Chemical Society Vol. 138; no. 45; pp. 14868 - 14871
Main Authors Ting, Chi P, Xu, Gong, Zeng, Xianhuang, Maimone, Thomas J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.11.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Cyclohexanones - chemical synthesis
Cyclohexanones - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Terpenes - chemical synthesis
CYTOCHROME-P450
NATURAL-PRODUCT SYNTHESIS
PENICILLIUM
POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS
TERRETONIN BIOSYNTHESIS
CONSTRUCTION
ANDRASTIN
POLYKETIDE-TERPENOID METABOLITE
ASPERGILLUS-TERREUS
CYCLIZATION
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Summary:Synthetic pathways to complex meroterpenes derived from 3,5-dimethylorsellinic acid (DMOA) and farnesyl pyrophosphate have not been reported despite heavy biosynthetic and medicinal interest. Herein we report the first total synthesis of berkeleyone A, a potential gateway compound to a plethora of fungal-derived meroterpenes, in 13 steps. In addition, we have further developed a novel annulation reaction for the synthesis of hydroxylated 1,3-cyclohexadiones in a single step.
Bibliography:NIH RePORTER
National Science Foundation
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b10397