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

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

doi:10.1055/s-0035-1561948

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

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

Department of Applied Chemistry

Research output: Contribution to journal › Article

7 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
Journal	Synthesis (Germany)
DOIs	https://doi.org/10.1055/s-0035-1561948
Publication status	Accepted/In press - 2016 Feb 23

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Keywords

alkaloid
allylic compound
diol
sigmatropic rearrangement
total synthesis

ASJC Scopus subject areas

Organic Chemistry
Catalysis

Cite this

Nakayama, Y., Maeda, Y., Hama, N., Satou, T., & Chida, N. (Accepted/In press). Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement. Synthesis (Germany). https://doi.org/10.1055/s-0035-1561948

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Access to Document

10.1055/s-0035-1561948