Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine

Roderick W. Bates; Joseph A. Nemeth; Robert H. Snell

doi:10.1055/s-2008-1066985

Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine

Roderick W. Bates, Joseph A. Nemeth, Robert H. Snell

Nanyang Technological University

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

41 Citations (Scopus)

Abstract

Isoxazolidines have been prepared in a stereoselective manner by treatment of allenic hydroxylamines with silver(I). This methodology has been used in a short synthesis of the alkaloid (+)-sedamine.

Original language	English
Pages (from-to)	1033-1038
Number of pages	6
Journal	Synthesis
Issue number	7
DOIs	https://doi.org/10.1055/s-2008-1066985
Publication status	Published - Apr 1 2008
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

Alkaloids
Allenes
Cyclisation
Heterocycles
Stereoselectivity

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10.1055/s-2008-1066985

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title = "Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine",

abstract = "Isoxazolidines have been prepared in a stereoselective manner by treatment of allenic hydroxylamines with silver(I). This methodology has been used in a short synthesis of the alkaloid (+)-sedamine.",

keywords = "Alkaloids, Allenes, Cyclisation, Heterocycles, Stereoselectivity",

author = "Bates, {Roderick W.} and Nemeth, {Joseph A.} and Snell, {Robert H.}",

year = "2008",

month = apr,

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doi = "10.1055/s-2008-1066985",

language = "English",

pages = "1033--1038",

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AU - Bates, Roderick W.

AU - Nemeth, Joseph A.

AU - Snell, Robert H.

PY - 2008/4/1

Y1 - 2008/4/1

N2 - Isoxazolidines have been prepared in a stereoselective manner by treatment of allenic hydroxylamines with silver(I). This methodology has been used in a short synthesis of the alkaloid (+)-sedamine.

AB - Isoxazolidines have been prepared in a stereoselective manner by treatment of allenic hydroxylamines with silver(I). This methodology has been used in a short synthesis of the alkaloid (+)-sedamine.

KW - Alkaloids

KW - Allenes

KW - Cyclisation

KW - Heterocycles

KW - Stereoselectivity

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JF - Synthesis

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ER -

Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine

Abstract

ASJC Scopus Subject Areas

Keywords

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