title: Studies in marine polypropionate synthesis: total synthesis of (-)-baconipyrone C.
abstract: [reaction--see text] An asymmetric total synthesis of the unusual siphonariid metabolite, (-)-baconipyrone C (3), is described. Key steps included a tin(II)-mediated aldol coupling for the preparation of the carboxylic acid 17 and two different boron-mediated aldol additions leading to alcohol 8. Ester formation using modified Yamaguchi conditions gave 24, leading on PMB deprotection to (-)-baconipyrone C.
authors.affiliation: University Chemical Laboratory, Lensfield Road, Cambridge, UK. ip100@cus.cam.ac.uk
authors.forename: I
authors.initials: I
authors.lastname: Paterson
authors.forename: D Y
authors.initials: DY
authors.lastname: Chen
authors.forename: J L
authors.initials: JL
authors.lastname: Aceña
authors.forename: A S
authors.initials: AS
authors.lastname: Franklin
mesh_terms: D000818:Animals; D001685:Biological Factors / Q000138:chemical synthesis / Q000737:chemistry; D008386:Marine Biology; D008974:Mollusca / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D011422:Propionates / Q000138:chemical synthesis / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001685:Biological Factors; D011108:Polymers; D011422:Propionates; D011753:Pyrones; C410203:baconipyrone C