4.8 Article

Versatile Construction of 6-Substituted cis-2,8-Dioxabicyclo[3.3.0]octan-3-ones: Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 21, 页码 7192-7195

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AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b04265

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资金

  1. NSF [CHE1265964]
  2. National Research Foundation of Korea [NRF-2015R1A2A1A15056116]
  3. NIH
  4. [1F31GM113494]
  5. Direct For Mathematical & Physical Scien
  6. 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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