title: A concise approach for the synthesis of bitungolides: total syntheses of (-)-bitungolide B & E.
abstract: The first total synthesis of (-)-bitungolide B and a second-generation total synthesis of (-)-bitungolide E are described. The cornerstone of the approach comprises a convergent and flexible route involving Brown crotylation, highly diastereoselective substrate controlled Paterson anti-aldol reaction, hydroxyl-directed 1,3-syn/anti reduction, Barton-McCombie deoxygenation and RCM reactions. Via this route, a common intermediate 13 is readily accessible for the synthesis of the family of bitungolides A-E and franklinolides A-C.
authors.affiliation: Fine Chemicals Laboratory, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India. subhash@iict.res.in.
authors.forename: K Mahender
authors.initials: KM
authors.lastname: Reddy
authors.forename: J
authors.initials: J
authors.lastname: Shashidhar
authors.forename: Subhash
authors.initials: S
authors.lastname: Ghosh
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D007202:Indicators and Reagents; D007659:Ketones; D011753:Pyrones; C000596941:bitungolide B; C528466:bitungolide F