title: Stereoselective synthesis of the tetrahydropyran core of polycarvernoside A.
abstract: [reaction: see text] A concise and stereoselective synthesis of the tetrasubstituted tetrahydropyran core of polycavernoside A was achieved in 55% overall yield from 3-benzyloxypropanal. A stereoselective allyl transfer reaction was used in the synthesis of enol ether 18 followed by a TFA-mediated cyclization to create the three new asymmetric centers in the tetrahydropyran with complete stereocontrol in a single-pot process.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Conor S
authors.initials: CS
authors.lastname: Barry
authors.forename: Nick
authors.initials: N
authors.lastname: Bushby
authors.forename: John R
authors.initials: JR
authors.lastname: Harding
authors.forename: Christine L
authors.initials: CL
authors.lastname: Willis
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D000461:Rhodophyta / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004187:Disaccharides; D018942:Macrolides; D011714:Pyrans; C121303:polycavernoside A