Synthesis of 5-epi-desosamine via a stereoselective intramolecular N-sulfinyl diels-alder cycloaddition

Stacy W. Remiszewski; Robert R. Whittle; Steven M. Weinreb

doi:10.1021/jo00191a049

Synthesis of 5-epi-desosamine via a stereoselective intramolecular N-sulfinyl diels-alder cycloaddition

Stacy W. Remiszewski, Robert R. Whittle, Steven M. Weinreb

Chemistry

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36 Scopus citations

Abstract

S-epi-Desosamine (2) has been synthesized in six steps from diene alcohol 3 through a key intramolecular IV-sulfinyl dienophile Diels-Alder process which establishes the relative stereochemistry of the three chiral centers of the amino sugar.

Original language	English (US)
Pages (from-to)	3243-3244
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	49
Issue number	17
DOIs	https://doi.org/10.1021/jo00191a049
State	Published - Mar 1984

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00191a049

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title = "Synthesis of 5-epi-desosamine via a stereoselective intramolecular N-sulfinyl diels-alder cycloaddition",

abstract = "S-epi-Desosamine (2) has been synthesized in six steps from diene alcohol 3 through a key intramolecular IV-sulfinyl dienophile Diels-Alder process which establishes the relative stereochemistry of the three chiral centers of the amino sugar.",

author = "Remiszewski, {Stacy W.} and Whittle, {Robert R.} and Weinreb, {Steven M.}",

year = "1984",

month = mar,

doi = "10.1021/jo00191a049",

language = "English (US)",

volume = "49",

pages = "3243--3244",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

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T1 - Synthesis of 5-epi-desosamine via a stereoselective intramolecular N-sulfinyl diels-alder cycloaddition

AU - Remiszewski, Stacy W.

AU - Whittle, Robert R.

AU - Weinreb, Steven M.

PY - 1984/3

Y1 - 1984/3

N2 - S-epi-Desosamine (2) has been synthesized in six steps from diene alcohol 3 through a key intramolecular IV-sulfinyl dienophile Diels-Alder process which establishes the relative stereochemistry of the three chiral centers of the amino sugar.

AB - S-epi-Desosamine (2) has been synthesized in six steps from diene alcohol 3 through a key intramolecular IV-sulfinyl dienophile Diels-Alder process which establishes the relative stereochemistry of the three chiral centers of the amino sugar.

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DO - 10.1021/jo00191a049

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

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Synthesis of 5-epi-desosamine via a stereoselective intramolecular N-sulfinyl diels-alder cycloaddition

Abstract

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