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

17 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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10.1016/j.tet.2014.12.018

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title = "Total synthesis of (-)-rhazinilam using 1,3-dipolar cycloaddition of optically active m{\"u}nchnone intermediate",

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

keywords = "1,3-Dipolar cycloaddition, Alkaloids, M{\"u}nchnone, Total synthesis",

author = "Kenji Sugimoto and Yuta Miyakawa and Hidetoshi Tokuyama",

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doi = "10.1016/j.tet.2014.12.018",

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T1 - Total synthesis of (-)-rhazinilam using 1,3-dipolar cycloaddition of optically active münchnone intermediate

AU - Sugimoto, Kenji

AU - Miyakawa, Yuta

AU - Tokuyama, Hidetoshi

N1 - Funding Information: This work was financially supported by the Cabinet Office, Government of Japan through its ‘Funding Program for Next Generation World-Leading Researchers ’ ( LS008 ) and a Grant-in-aid for Scientific Research (A) ( 26253001 ), JSPS . Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

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.

AB - 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.

KW - 1,3-Dipolar cycloaddition

KW - Alkaloids

KW - Münchnone

KW - Total synthesis

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M3 - Article

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JO - Tetrahedron

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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