title: Enantioselective Total Synthesis of (+)-Neostenine.
abstract: A chirality transfer approach using acyclic polyol intermediates for the synthesis of (+)-neostenine (1) has been developed. The sequential Overman/Claisen rearrangement of an allylic 1,2-diol was especially useful, installing two contiguous stereocenters with complete diastereoselectivity in a one-pot sequence. The SmI2-mediated cyclization and the subsequent chemoselective reduction of a lactam moiety accomplished the first enantioselective total synthesis of (+)-neostenine (1).
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Yasuaki
authors.initials: Y
authors.lastname: Nakayama
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Yuichiro
authors.initials: Y
authors.lastname: Maeda
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Kotatsu
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Ruriko
authors.initials: R
authors.lastname: Sekiya
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Masato
authors.initials: M
authors.lastname: Ichiki
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan. takaakis@applc.keio.ac.jp.
authors.forename: Takaaki
authors.initials: T
authors.lastname: Sato
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan. chida@applc.keio.ac.jp.
authors.forename: Noritaka
authors.initials: N
authors.lastname: Chida
keywords: alkaloid; allylic compound; diol; sigmatropic rearrangement; total synthesis