title: Enantioselective construction of cis-2,6-disubstituted dihydropyrans: total synthesis of (-)-centrolobine.
abstract: This paper presents a simple and efficient route to chiral cis-6-substituted 2-(2-hydroxyethyl)-5,6-dihydro-2H-pyrans, a versatile chiral building block. The strategy is based on three key transformations: enantioselective hetero-Diels-Alder (HDA) reaction of aldehyde with Danishefsky's diene, selective reduction of carbonyl function, and Claisen or related rearrangement. The synthetic utility of the methodology is illustrated by total synthesis of antibiotic (-)-centolobine.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland.
authors.forename: Wojciech
authors.initials: W
authors.lastname: Chaładaj
authors.forename: Rafał
authors.initials: R
authors.lastname: Kowalczyk
authors.forename: Janusz
authors.initials: J
authors.lastname: Jurczak
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000447:Aldehydes; D009942:Organometallic Compounds; D011714:Pyrans; C432457:centrolobin