General Access to Concave-Substituted cis -Dioxabicyclo[3.3.0]octanones: Enantioselective Total Syntheses of Macfarlandin C and Dendrillolide A.

Autor:	Allred TK; Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025, United States., Dieskau AP; Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025, United States., Zhao P; Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025, United States., Lackner GL; Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025, United States., Overman LE; Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025, United States.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2020 Dec 04; Vol. 85 (23), pp. 15532-15551. Date of Electronic Publication: 2020 Nov 16.
DOI:	10.1021/acs.joc.0c02273
Abstrakt:	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.
Databáze:	MEDLINE
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