Modular approach to pseudo-neoclerodanes as designer κ-opioid ligands

Alexander M. Sherwood; Samuel E. Williamson; Rachel S. Crowley; Logan M. Abbott; Victor W. Day; Thomas E. Prisinzano

doi:10.1021/acs.orglett.7b02684

Modular approach to pseudo-neoclerodanes as designer κ-opioid ligands

Alexander M. Sherwood, Samuel E. Williamson, Rachel S. Crowley, Logan M. Abbott, Victor W. Day, Thomas E. Prisinzano

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

12 Scopus citations

Abstract

Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of functionality about the target molecule to provide access to molecular features on salvinorin A otherwise unattainable by semisynthesis. Using this approach, a potent pseudo-neoclerodane κ-opioid receptor ligand (2) has been realized.

Original language	English
Pages (from-to)	5414-5417
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.7b02684
State	Published - Oct 6 2017

Bibliographical note

Funding Information:
This work was supported by DA018151 and GM1385 (to T.E.P.), GM008545 (to S.E.W. and R.S.C.), AFPE Predoctoral Fellowship in Pharmaceutical Sciences (to R.S.C.), and NSF-MRI Grant CHE-0923449 (V.W.D.). Support for the NMR instrumentation was provided by NIH Shared Instrumentation Grant #S10RR024664 and NSF Major Research Instrumentation Grant #0320648.

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Modular approach to pseudo-neoclerodanes as designer κ-opioid ligands",

abstract = "Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of functionality about the target molecule to provide access to molecular features on salvinorin A otherwise unattainable by semisynthesis. Using this approach, a potent pseudo-neoclerodane κ-opioid receptor ligand (2) has been realized.",

author = "Sherwood, {Alexander M.} and Williamson, {Samuel E.} and Crowley, {Rachel S.} and Abbott, {Logan M.} and Day, {Victor W.} and Prisinzano, {Thomas E.}",

note = "Funding Information: This work was supported by DA018151 and GM1385 (to T.E.P.), GM008545 (to S.E.W. and R.S.C.), AFPE Predoctoral Fellowship in Pharmaceutical Sciences (to R.S.C.), and NSF-MRI Grant CHE-0923449 (V.W.D.). Support for the NMR instrumentation was provided by NIH Shared Instrumentation Grant #S10RR024664 and NSF Major Research Instrumentation Grant #0320648. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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AU - Sherwood, Alexander M.

AU - Williamson, Samuel E.

AU - Crowley, Rachel S.

AU - Abbott, Logan M.

AU - Day, Victor W.

AU - Prisinzano, Thomas E.

N1 - Funding Information: This work was supported by DA018151 and GM1385 (to T.E.P.), GM008545 (to S.E.W. and R.S.C.), AFPE Predoctoral Fellowship in Pharmaceutical Sciences (to R.S.C.), and NSF-MRI Grant CHE-0923449 (V.W.D.). Support for the NMR instrumentation was provided by NIH Shared Instrumentation Grant #S10RR024664 and NSF Major Research Instrumentation Grant #0320648. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/10/6

Y1 - 2017/10/6

N2 - Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of functionality about the target molecule to provide access to molecular features on salvinorin A otherwise unattainable by semisynthesis. Using this approach, a potent pseudo-neoclerodane κ-opioid receptor ligand (2) has been realized.

AB - Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of functionality about the target molecule to provide access to molecular features on salvinorin A otherwise unattainable by semisynthesis. Using this approach, a potent pseudo-neoclerodane κ-opioid receptor ligand (2) has been realized.

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Modular approach to pseudo-neoclerodanes as designer κ-opioid ligands

Abstract

Bibliographical note

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