Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 21, Pages 7192-7195Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b04265
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Funding
- NSF [CHE1265964]
- National Research Foundation of Korea [NRF-2015R1A2A1A15056116]
- NIH
- [1F31GM113494]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1429735] Funding Source: National Science Foundation
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A short enantioselective synthesis of 6-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-ones is described. The pivotal step is coupling of a tertiary radical generated directly from a tertiary alcohol with a 3-chloro-5-alkoxybutenolide. This strategy is applied toward scalable 14-15 step syntheses of three rearranged spongian diterpenoids: cheloviolenes A and B and dendrillolide C.
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