Enantioselective Total Synthesis of (+)-Neostenine.

Nakayama, Yasuaki; Maeda, Yuichiro; Kotatsu, Masayuki; Sekiya, Ruriko; Ichiki, Masato; Sato, Takaaki; Chida, Noritaka

Nakayama, Yasuaki; Maeda, Yuichiro; Kotatsu, Masayuki; Sekiya, Ruriko; Ichiki, Masato; Sato, Takaaki; Chida, Noritaka.

Afiliação

Nakayama Y; Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Maeda Y; Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Kotatsu M; Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Sekiya R; Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Ichiki M; Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Sato T; 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.
Chida N; 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.

Chemistry ; 22(10): 3300-3303, 2016 Mar 01.

Article em En | MEDLINE | ID: mdl-26756545

ABSTRACT

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).

Palavras-chave

alkaloid; allylic compound; diol; sigmatropic rearrangement; total synthesis

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Chemistry Assunto da revista: QUIMICA Ano de publicação: 2016 Tipo de documento: Article País de afiliação: Japão

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