Journal of Organic Chemistry p. 5269 - 5281 (2014)
Update date:2022-08-03
Topics:
Hume, Paul A.
Furkert, Daniel. P.
Brimble, Margaret A.
A full account of the enantioselective total synthesis of virgatolide B is reported. Key features of the synthesis include an sp3-sp2 Suzuki-Miyaura cross-coupling of a β-trifluoroboratoamide with an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction. Intramolecular hydrogen bonding governed the regioselectivity of the key spiroketalization step, affording the natural product as a single regioisomer.
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