Synthetic studies of neoclerodane diterpenes from Salvia divinorum: Selective modification of the furan ring

Wayne W. Harding; Matthew Schmidt; Kevin Tidgewell; Pavitra Kannan; Kenneth G. Holden; Christina M. Dersch; Richard B. Rothman; Thomas E. Prisinzano

doi:10.1016/j.bmcl.2006.03.062

Synthetic studies of neoclerodane diterpenes from Salvia divinorum: Selective modification of the furan ring

Wayne W. Harding, Matthew Schmidt, Kevin Tidgewell, Pavitra Kannan, Kenneth G. Holden, Christina M. Dersch, Richard B. Rothman, Thomas E. Prisinzano

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

41 Scopus citations

Abstract

A synthetic sequence has been developed to selectively functionalize the furan ring of the natural product salvinorin A (2a). The synthetic routes described convert the furan ring in 2a into an N-sulfonylpyrrole, oxazole or an oxadiazole. In addition, a procedure has been found to remove the furan skeleton completely. Biological results indicate that replacement of the furan ring with an N-sulfonylpyrrole leads to reduced affinity and efficacy at κ opioid receptors.

Original language	English
Pages (from-to)	3170-3174
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	16
Issue number	12
DOIs	https://doi.org/10.1016/j.bmcl.2006.03.062
State	Published - Jun 15 2006

Bibliographical note

Funding Information:
This work was supported by National Institutes of Health, National Institute on Drug Abuse Grant DA18151 (to TEP), and in part by the Intramural Research Program of the NIH, NIDA. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa, for mass spectral analysis.

Funding

This work was supported by National Institutes of Health, National Institute on Drug Abuse Grant DA18151 (to TEP), and in part by the Intramural Research Program of the NIH, NIDA. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa, for mass spectral analysis.

Funders	Funder number
National Institutes of Health (NIH)
National Institute on Drug Abuse	R01DA018151

Keywords

Heterocycle
Kappa
Opioid
Salvia divinorum
Salvinorin A

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2006.03.062

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title = "Synthetic studies of neoclerodane diterpenes from Salvia divinorum: Selective modification of the furan ring",

abstract = "A synthetic sequence has been developed to selectively functionalize the furan ring of the natural product salvinorin A (2a). The synthetic routes described convert the furan ring in 2a into an N-sulfonylpyrrole, oxazole or an oxadiazole. In addition, a procedure has been found to remove the furan skeleton completely. Biological results indicate that replacement of the furan ring with an N-sulfonylpyrrole leads to reduced affinity and efficacy at κ opioid receptors.",

keywords = "Heterocycle, Kappa, Opioid, Salvia divinorum, Salvinorin A",

author = "Harding, {Wayne W.} and Matthew Schmidt and Kevin Tidgewell and Pavitra Kannan and Holden, {Kenneth G.} and Dersch, {Christina M.} and Rothman, {Richard B.} and Prisinzano, {Thomas E.}",

note = "Funding Information: This work was supported by National Institutes of Health, National Institute on Drug Abuse Grant DA18151 (to TEP), and in part by the Intramural Research Program of the NIH, NIDA. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa, for mass spectral analysis.",

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T2 - Selective modification of the furan ring

AU - Harding, Wayne W.

AU - Schmidt, Matthew

AU - Tidgewell, Kevin

AU - Kannan, Pavitra

AU - Holden, Kenneth G.

AU - Dersch, Christina M.

AU - Rothman, Richard B.

AU - Prisinzano, Thomas E.

N1 - Funding Information: This work was supported by National Institutes of Health, National Institute on Drug Abuse Grant DA18151 (to TEP), and in part by the Intramural Research Program of the NIH, NIDA. The authors also thank Vic Parcell and Lynn Teesch of the High Resolution Mass Spectrometry Facility, University of Iowa, for mass spectral analysis.

PY - 2006/6/15

Y1 - 2006/6/15

N2 - A synthetic sequence has been developed to selectively functionalize the furan ring of the natural product salvinorin A (2a). The synthetic routes described convert the furan ring in 2a into an N-sulfonylpyrrole, oxazole or an oxadiazole. In addition, a procedure has been found to remove the furan skeleton completely. Biological results indicate that replacement of the furan ring with an N-sulfonylpyrrole leads to reduced affinity and efficacy at κ opioid receptors.

AB - A synthetic sequence has been developed to selectively functionalize the furan ring of the natural product salvinorin A (2a). The synthetic routes described convert the furan ring in 2a into an N-sulfonylpyrrole, oxazole or an oxadiazole. In addition, a procedure has been found to remove the furan skeleton completely. Biological results indicate that replacement of the furan ring with an N-sulfonylpyrrole leads to reduced affinity and efficacy at κ opioid receptors.

KW - Heterocycle

KW - Kappa

KW - Opioid

KW - Salvia divinorum

KW - Salvinorin A

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 12

ER -

Synthetic studies of neoclerodane diterpenes from Salvia divinorum: Selective modification of the furan ring

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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