Perchloric acid induced epimerisation of the thevinones: An improved synthesis of 7β-dihydrothevinones

Ian Derrick; Andrew Coop; Sali M. Al-Mousawi; Stephen M. Husbands; John W. Lewis

doi:10.1016/S0040-4039(00)01300-9

Perchloric acid induced epimerisation of the thevinones: An improved synthesis of 7β-dihydrothevinones

Ian Derrick, Andrew Coop, Sali M. Al-Mousawi, Stephen M. Husbands, John W. Lewis

University of Bristol

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

6 Citations (SciVal)

Abstract

The region above and away from C7 in the orvinols is known to be of particular importance in determining the μ-opioid receptor profile of this important class of opioids. However it has been difficult to explore this site due to the relative inaccessibility of 7β-substituted compounds. Here we report that perchloric acid induced epimerisation of the 7α-ketones (dihydrothevinones) allows considerably improved access to a series of β-ketones (β-dihydrothevinones). The extent of epimerisation of the 7α-ketone is determined by the degree of steric bulk in both the 6,14-bridge and in the ketone side chain.

Original language	English
Pages (from-to)	7571-7576
Number of pages	6
Journal	Tetrahedron Letters
Volume	41
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4039(00)01300-9
Publication status	Published - 23 Sept 2000

Keywords

7β-dihydrothevinones
Epimerisation
Opioids
Thevinones

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)01300-9

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abstract = "The region above and away from C7 in the orvinols is known to be of particular importance in determining the μ-opioid receptor profile of this important class of opioids. However it has been difficult to explore this site due to the relative inaccessibility of 7β-substituted compounds. Here we report that perchloric acid induced epimerisation of the 7α-ketones (dihydrothevinones) allows considerably improved access to a series of β-ketones (β-dihydrothevinones). The extent of epimerisation of the 7α-ketone is determined by the degree of steric bulk in both the 6,14-bridge and in the ketone side chain.",

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T2 - An improved synthesis of 7β-dihydrothevinones

AU - Derrick, Ian

AU - Coop, Andrew

AU - Al-Mousawi, Sali M.

AU - Husbands, Stephen M.

AU - Lewis, John W.

PY - 2000/9/23

Y1 - 2000/9/23

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AB - The region above and away from C7 in the orvinols is known to be of particular importance in determining the μ-opioid receptor profile of this important class of opioids. However it has been difficult to explore this site due to the relative inaccessibility of 7β-substituted compounds. Here we report that perchloric acid induced epimerisation of the 7α-ketones (dihydrothevinones) allows considerably improved access to a series of β-ketones (β-dihydrothevinones). The extent of epimerisation of the 7α-ketone is determined by the degree of steric bulk in both the 6,14-bridge and in the ketone side chain.

KW - 7β-dihydrothevinones

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KW - Thevinones

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DO - 10.1016/S0040-4039(00)01300-9

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Perchloric acid induced epimerisation of the thevinones: An improved synthesis of 7β-dihydrothevinones

Abstract

Keywords

ASJC Scopus subject areas

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