Total Synthesis of (-)-Antroalbocin A Enabled by a Strain Release-Controlled Photochemical 1,3-Acyl Shift.
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DOI: 10.1021/acs.orglett.2c02347
Abstract: The first bioinspired, enantioselective, and protecting group free total synthesis of the antibacterial sesquiterpenoid (-)-antroalbocin A (1) has been achieved in 12 steps (5.4% overall yield) from dimedone. An organocatalytic Robinson annulation gave rapid access… read more here.
Keywords: total synthesis; antroalbocin; acyl shift; acyl ... See more keywords
Oxidative Dearomatization and Sigmatropic 1,3-Acyl Shift in Excited State: Aromatics to Embellished cis-Hydrindanes
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DOI: 10.1055/s-0037-1611367
Abstract: A stereoselective synthetic route to embellished cis-hydrindanes from simple aromatic precursors is described. Oxidative dearomatization, ring expansion, and photochemical 1,3-acyl shift are the key features of our approach. Oxidative dearomatization of o-(hydroxymethyl)phenols followed by π4s… read more here.
Keywords: acyl shift; oxidative dearomatization; embellished cis; cis hydrindanes ... See more keywords