title: Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family.
abstract: A simple, highly diastereoselective, Lewis acid catalyzed Friedel-Crafts coupling of a cyclic allylic alcohol with resorcinol derivatives has been developed. The method was applied for the enantiospecific total syntheses of structurally diverse natural products such as machaeriol-D, Δ(8)-THC, Δ(9)-THC, epi-perrottetinene and their analogues. Synthesis of both natural products and their enantiomers has been achieved with high atom economy, in a protecting group free manner and in less than 6 steps, the longest linear sequence, in a very good overall yield starting from R-(+) and S-(-)-limonene.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, India. ddethe@iitk.ac.in.
authors.forename: Dattatraya H
authors.initials: DH
authors.lastname: Dethe
authors.forename: Rohan D
authors.initials: RD
authors.lastname: Erande
authors.forename: Samarpita
authors.initials: S
authors.lastname: Mahapatra
authors.forename: Saikat
authors.initials: S
authors.lastname: Das
authors.forename: Vijay
authors.initials: V
authors.lastname: Kumar B