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

応用化学科

研究成果: Article › 査読

20 被引用数 (Scopus)

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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.

本文言語	English
論文番号	ss-2016-c0050-st
ページ（範囲）	1647-1654
ページ数	8
ジャーナル	Synthesis (Germany)
巻	48
号	11
DOI	https://doi.org/10.1055/s-0035-1561948
出版ステータス	Published - 2016 6月 2

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有機化学

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AU - Maeda, Yuichiro

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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.

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KW - allylic compound

KW - diol

KW - sigmatropic rearrangement

KW - total synthesis

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

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