Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 23, Pages 15532-15551Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02273
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Funding
- National Science Foundation [CHE-1265964, CHE-1661612]
- National Institute of General Medical Sciences [R01GM098601]
- ACS Organic Chemistry Division
- German Academic Exchange Service (DAAD)
- NSF
- NIH
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The evolution of a strategy to access the family of rearranged spongian diterpenoids harboring a concave-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-one fragment is described. The approach involves late-stage fragment coupling of a tertiary-carbon radical and an electron-deficient double bond to form vicinal quaternary and tertiary stereocenters with high fidelity. A stereoselective Mukaiyama hydration is the key step in the subsequent elaboration of the cis-2,8-dioxabicyclo[3.3.0]octan-3-one moiety. This strategy was utilized in enantioselective total syntheses of (-)-macfarlandin C and (+)-dendrillolide A. An efficient construction of enantiopure tetramethyloctahydronaphthalenes was developed during the construction of (-)-macfarlandin C.
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