Enantioselective Total Synthesis of (+)-Neostenine

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

doi:10.1002/chem.201600058

Enantioselective Total Synthesis of (+)-Neostenine

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

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).

Original language	English
Pages (from-to)	3300-3303
Number of pages	4
Journal	Chemistry - A European Journal
Volume	22
Issue number	10
DOIs	https://doi.org/10.1002/chem.201600058
Publication status	Published - 2016 Mar 1

Keywords

alkaloid
allylic compound
diol
sigmatropic rearrangement
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201600058

Cite this

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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).",

keywords = "alkaloid, allylic compound, diol, sigmatropic rearrangement, total synthesis",

author = "Yasuaki Nakayama and Yuichiro Maeda and Masayuki Kotatsu and Ruriko Sekiya and Masato Ichiki and Takaaki Sato and Noritaka Chida",

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AU - Nakayama, Yasuaki

AU - Maeda, Yuichiro

AU - Kotatsu, Masayuki

AU - Sekiya, Ruriko

AU - Ichiki, Masato

AU - Sato, Takaaki

AU - Chida, Noritaka

N1 - Funding Information: This research was supported byaGrant-in-Aid for Scientific Research (B) from MEXT (26288018), and the Shorai Foundation for Science and Technology. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2016/3/1

Y1 - 2016/3/1

N2 - 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).

AB - 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).

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KW - allylic compound

KW - diol

KW - sigmatropic rearrangement

KW - total synthesis

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Enantioselective Total Synthesis of (+)-Neostenine

Abstract

Keywords

ASJC Scopus subject areas

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