Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 15, Pages 6006-6017Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c02150
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Funding
- University of Illinois
- National Institute of General Medical Sciences, National Institute of Health [GM 124480]
- Bristol Myers Squibb
- Eli Lilly
- Amgen
- FMC
- Roy J. Carver Charitable Trust, Muscatine, Iowa, USA
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This article describes a method for synthesizing sesquiterpene compounds and explains stereoselectivity through computational modeling studies, leading to stereochemical reassignments of the pycnidione subclass and providing new insights into the biosynthesis of these natural products.
The sesquiterpene-tropolones belong to a distinctive structural class of meroterpene natural products with impressive biological activities, including anticancer, antifungal, antimalarial, and antibacterial. In this article, we describe a concise, modular, and cycloaddition-based approach to a series of sesquiterpene mono- and bistropolones, including (-)-epolone B, (+)-isoepolone B, (+/-)-dehy-droxypycnidione, and (-)-10-epi-pycnidione. Alongside the development of a general strategy to access this unique family of metabolites were computational modeling studies that justified the diastereoselectivity observed during key cycloadditions. Ultimately, these studies prompted stereochemical reassignments of the pycnidione subclass and shed additional light on the biosynthesis of these remarkable natural products.
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