Substrate-controlled asymmetric total synthesis and structure revision of (+)-itomanallene a

Abstract

Chemical equation presented In control: The first asymmetric total synthesis of (-)-itomanallene A (revised structure) has been accomplished starting from commercially available (S)-glycidol in a substrate-controlled fashion. The approach yields α,α' -cis- or α,α' -transtetrahydrofuran isomers by intramolecular alkylation with either an amide enolate or a nitrile anion, respectively. © 2010 Wlley-VCH Verlag GmbH & Co. KGaA.