Total Synthesis of (-)-Stemoamide by Sequential Overman/Claisen Rearrangement

Yasuaki Nakayama; Yuichiro Maeda; Naoto Hama; Takaaki Sato; Noritaka Chida

doi:10.1055/s-0035-1561948

Total Synthesis of (-)-Stemoamide by Sequential Overman/Claisen Rearrangement

Yasuaki Nakayama, Yuichiro Maeda, Naoto Hama, Takaaki Sato, Noritaka Chida

Department of Applied Chemistry

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

15 Citations (Scopus)

Abstract

The enantioselective total synthesis of (-)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.

Original language	English
Article number	ss-2016-c0050-st
Pages (from-to)	1647-1654
Number of pages	8
Journal	Synthesis (Germany)
Volume	48
Issue number	11
DOIs	https://doi.org/10.1055/s-0035-1561948
Publication status	Published - 2016 Jun 2

Keywords

alkaloid
allylic compound
diol
sigmatropic rearrangement
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0035-1561948

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title = "Total Synthesis of (-)-Stemoamide by Sequential Overman/Claisen Rearrangement",

abstract = "The enantioselective total synthesis of (-)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.",

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author = "Yasuaki Nakayama and Yuichiro Maeda and Naoto Hama and Takaaki Sato and Noritaka Chida",

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AU - Nakayama, Yasuaki

AU - Maeda, Yuichiro

AU - Hama, Naoto

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2016/6/2

Y1 - 2016/6/2

N2 - The enantioselective total synthesis of (-)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.

AB - The enantioselective total synthesis of (-)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.

KW - alkaloid

KW - allylic compound

KW - diol

KW - sigmatropic rearrangement

KW - total synthesis

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JF - Synthesis (Germany)

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ER -

Total Synthesis of (-)-Stemoamide by Sequential Overman/Claisen Rearrangement

Abstract

Keywords

ASJC Scopus subject areas

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