Total synthesis of (-)-rhazinilam using 1,3-dipolar cycloaddition of optically active münchnone intermediate

Kenji Sugimoto; Yuta Miyakawa; Hidetoshi Tokuyama

doi:10.1016/j.tet.2014.12.018

Total synthesis of (-)-rhazinilam using 1,3-dipolar cycloaddition of optically active münchnone intermediate

Kenji Sugimoto, Yuta Miyakawa, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

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

16 Citations (Scopus)

Abstract

A concise stereocontrolled total synthesis of (-)-rhazinilam was achieved by the regioselective 1,3-dipolar cycloaddition of a fully elaborated optically active münchnone intermediate prepared from d-aspartic acid dimethyl ester. The regiochemistry of the 1,3-dipolar cycloaddition of münchnone intermediate to various arylacetylenes was also investigated.

Original language	English
Pages (from-to)	3619-3624
Number of pages	6
Journal	Tetrahedron
Volume	71
Issue number	22
DOIs	https://doi.org/10.1016/j.tet.2014.12.018
Publication status	Published - 2015 Jun 3

Keywords

1,3-Dipolar cycloaddition
Alkaloids
Münchnone
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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AU - Sugimoto, Kenji

AU - Miyakawa, Yuta

AU - Tokuyama, Hidetoshi

PY - 2015/6/3

Y1 - 2015/6/3

N2 - A concise stereocontrolled total synthesis of (-)-rhazinilam was achieved by the regioselective 1,3-dipolar cycloaddition of a fully elaborated optically active münchnone intermediate prepared from d-aspartic acid dimethyl ester. The regiochemistry of the 1,3-dipolar cycloaddition of münchnone intermediate to various arylacetylenes was also investigated.

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KW - 1,3-Dipolar cycloaddition

KW - Alkaloids

KW - Münchnone

KW - Total synthesis

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JF - Tetrahedron

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