title: 2-Arylcyclopropylmethanol as a substitute for homoallyl aryl alcohol in the construction of cis-2,6-disubstituted tetrahydropyran: synthesis of (±)-centrolobine.
abstract: The application of 2-arylcyclopropylmethanols as substitutes to homoallyl aryl alcohols and their reactions with aliphatic aldehydes in the presence of SnCl4 in CH2Cl2 leads to an efficient Prins cyclization to generate cis-2,6-disubstituted tetrahydropyrans in high yields. The reaction is free from 2-oxonia-Cope rearrangement. This protocol was used to synthesize (±)-centrolobine in an overall 84% yield over three steps. The protocol holds promise for scaffold generation for medicinal chemistry exploitation.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India. vijendra@iitk.ac.in.
authors.forename: Veejendra K
authors.initials: VK
authors.lastname: Yadav
authors.forename: Ashish K
authors.initials: AK
authors.lastname: Verma
authors.forename: Piyush
authors.initials: P
authors.lastname: Kumar
authors.forename: Vijaykumar
authors.initials: V
authors.lastname: Hulikal
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis*
chemical_list: D000438:Alcohols; D003521:Cyclopropanes; D011714:Pyrans; C432457:centrolobin