A Concise Synthesis of Castanospermine by the Use of a Transannular Cyclization

Thomas Jensen; Mette Mikkelsen; Anne Lauritsen; Thomas Lars Andresen; Charlotte Held Gotfredsen; Robert Madsen

doi:10.1021/jo9019495

A Concise Synthesis of Castanospermine by the Use of a Transannular Cyclization

Thomas Jensen, Mette Mikkelsen, Anne Lauritsen, Thomas Lars Andresen, Charlotte Held Gotfredsen, Robert Madsen

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl alpha-D-glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyranoside, ring-closing olefin metathesis, and strain-release transannular cyclization to afford the indolizidine skeleton of the natural product.

Original language	English
Journal	Journal of Organic Chemistry
Volume	74
Issue number	22
Pages (from-to)	8886-8889
ISSN	0022-3263
DOIs	https://doi.org/10.1021/jo9019495
Publication status	Published - 2009

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title = "A Concise Synthesis of Castanospermine by the Use of a Transannular Cyclization",

abstract = "A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl alpha-D-glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyranoside, ring-closing olefin metathesis, and strain-release transannular cyclization to afford the indolizidine skeleton of the natural product.",

author = "Thomas Jensen and Mette Mikkelsen and Anne Lauritsen and Andresen, {Thomas Lars} and Gotfredsen, {Charlotte Held} and Robert Madsen",

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journal = "Journal of Organic Chemistry",

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AU - Jensen, Thomas

AU - Mikkelsen, Mette

AU - Lauritsen, Anne

AU - Andresen, Thomas Lars

AU - Gotfredsen, Charlotte Held

AU - Madsen, Robert

PY - 2009

Y1 - 2009

N2 - A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl alpha-D-glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyranoside, ring-closing olefin metathesis, and strain-release transannular cyclization to afford the indolizidine skeleton of the natural product.

AB - A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl alpha-D-glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyranoside, ring-closing olefin metathesis, and strain-release transannular cyclization to afford the indolizidine skeleton of the natural product.

U2 - 10.1021/jo9019495

DO - 10.1021/jo9019495

M3 - Journal article

C2 - 19856948

SN - 0022-3263

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SP - 8886

EP - 8889

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

A Concise Synthesis of Castanospermine by the Use of a Transannular Cyclization

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