Total synthesis of virgatolide B via exploitation of intramolecular hydrogen bonding.
A full account of the enantioselective total synthesis of virgatolide B is reported. Key features of the synthesis include an sp(3)-sp(2) 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.
Maurice Wilkins Centre for Molecular Biodiscovery, School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.
Paul A
PA
Hume
Daniel P
DP
Furkert
Margaret A
MA
Brimble
D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D013141:Spiro Compounds; C559533:virgatolide B