title: Highly stereocontrolled synthesis of trans-2,6-disubstituted-5-methyl-3,6-dihydropyrans: stereoselective synthesis of the bicyclic core of penostatin B.
abstract: An efficient, mild, and highly diastereoselective strategy for the synthesis of trans-2,6-disubstituted-5-methyl-3,6-dihydropyran ring systems has been developed starting from δ-hydroxy α-methyl α,β-unsaturated aldehydes and allyltrimethylsilane in the presence of a catalytic amount of ZnBr2 in a highly diastereoselective manner with excellent yield. The versatility of the above method was also demonstrated for the construction of the bicyclic core present in penostatin B in a concise and highly stereoselective manner.
authors.affiliation: Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology , Hyderabad 500 007, India.
authors.forename: D Srinivas
authors.initials: DS
authors.lastname: Reddy
authors.forename: Birakishore
authors.initials: B
authors.lastname: Padhi
authors.forename: Debendra K
authors.initials: DK
authors.lastname: Mohapatra
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D011714:Pyrans; C418128:penostatin B