Total synthesis of pawhuskin C: A directed ortho metalation approach

Jeffrey D. Neighbors; Maya S. Salnikova; David F. Wiemer

doi:10.1016/j.tetlet.2004.12.114

Total synthesis of pawhuskin C: A directed ortho metalation approach

Jeffrey D. Neighbors, Maya S. Salnikova, David F. Wiemer

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24 Scopus citations

Abstract

The total synthesis of the opioid modulator pawhuskin C has been accomplished in eight steps from methyl 3,5-dihydroxybenzoate. The key step in this sequence is a directed ortho metalation reaction conducted without protection of a benzylic alcohol and thus presumed to involve a formal dianion intermediate.

Original language	English (US)
Pages (from-to)	1321-1324
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2004.12.114
State	Published - Feb 21 2005

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.12.114

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title = "Total synthesis of pawhuskin C: A directed ortho metalation approach",

abstract = "The total synthesis of the opioid modulator pawhuskin C has been accomplished in eight steps from methyl 3,5-dihydroxybenzoate. The key step in this sequence is a directed ortho metalation reaction conducted without protection of a benzylic alcohol and thus presumed to involve a formal dianion intermediate.",

author = "Neighbors, {Jeffrey D.} and Salnikova, {Maya S.} and Wiemer, {David F.}",

note = "Funding Information: We thank Professor Gil Belofsky (University of Tulsa) for providing an authentic sample of pawhuskin C. Financial support from the Breast Cancer Research Program (DAMD17-01-1-0276 and DAMD17-02-1-0423) and the University of Iowa Graduate College is gratefully acknowledged.",

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doi = "10.1016/j.tetlet.2004.12.114",

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T2 - A directed ortho metalation approach

AU - Neighbors, Jeffrey D.

AU - Salnikova, Maya S.

AU - Wiemer, David F.

N1 - Funding Information: We thank Professor Gil Belofsky (University of Tulsa) for providing an authentic sample of pawhuskin C. Financial support from the Breast Cancer Research Program (DAMD17-01-1-0276 and DAMD17-02-1-0423) and the University of Iowa Graduate College is gratefully acknowledged.

PY - 2005/2/21

Y1 - 2005/2/21

N2 - The total synthesis of the opioid modulator pawhuskin C has been accomplished in eight steps from methyl 3,5-dihydroxybenzoate. The key step in this sequence is a directed ortho metalation reaction conducted without protection of a benzylic alcohol and thus presumed to involve a formal dianion intermediate.

AB - The total synthesis of the opioid modulator pawhuskin C has been accomplished in eight steps from methyl 3,5-dihydroxybenzoate. The key step in this sequence is a directed ortho metalation reaction conducted without protection of a benzylic alcohol and thus presumed to involve a formal dianion intermediate.

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DO - 10.1016/j.tetlet.2004.12.114

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EP - 1324

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Total synthesis of pawhuskin C: A directed ortho metalation approach

Abstract

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