Total Synthesis of Virgatolide B via Exploitation of Intramolecular Hydrogen Bonding
journal contributionposted on 06.06.2014, 00:00 by Paul A. Hume, Daniel. P. Furkert, Margaret A. Brimble
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.