title: Substrate-Controlled Asymmetric Total Synthesis and Structure Revision of (-)-Bisezakyne A.
abstract: The first asymmetric total synthesis and subsequent structure revision of (-)-bisezakyne A, a Laurencia C15 acetogenin from Alpysia oculifera, has been accomplished. Our substrate-controlled synthesis of this oxolane natural product features a highly stereoselective "protecting-group-dependent" intramolecular amide enolate alkylation strategy for the synthesis of the key 9,10-trans-9,12-cis-10-hydroxytetrahydrofuran intermediate through "nonchelate" control. In addition, our synthesis determined the absolute configuration of the halogenated marine natural product.
authors.affiliation: College of Pharmacy and Research Institute of Pharmaceutical Science and Technology (RIPST), Ajou University , Suwon 16499, Republic of Korea.
authors.forename: Iljin
authors.initials: I
authors.lastname: Shin
authors.affiliation: College of Pharmacy and Research Institute of Pharmaceutical Science and Technology (RIPST), Ajou University , Suwon 16499, Republic of Korea.
authors.forename: Dongjoo
authors.initials: D
authors.lastname: Lee
authors.affiliation: College of Pharmacy and Research Institute of Pharmaceutical Science and Technology (RIPST), Ajou University , Suwon 16499, Republic of Korea.
authors.forename: Hyoungsu
authors.initials: H
authors.lastname: Kim