title: Total synthesis of virgatolide B.
abstract: The first total synthesis of the benzannulated spiroketal virgatolide A is presented. Key features include sp(3)-sp(2) Suzuki coupling of an enantiomerically enriched β-trifluoroboratoamide and an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction followed by global deprotection/cyclization with regioselectivity governed by internal hydrogen bonding.
authors: School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
authors: Paul A
authors: PA
authors: Hume
authors: Daniel P
authors: DP
authors: Furkert
authors: Margaret A
authors: MA
authors: Brimble
mesh_terms: D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013098:Xylariales / Q000737:chemistry
chemical_list: D005663:Furans; D013141:Spiro Compounds; C520774:spiroketal; C559533:virgatolide B