Novel Synthesis of the Ortho Ester Derivative of 4,5-Epoxymorphinan

Novel Synthesis of the Ortho Ester Derivative of 4,5-Epoxymorphinan

A method was found for the novel synthesis of ortho ester derivatives that are potentially useful as selective ε opioid receptor ligands. An unexpected 17-(cyclopropylmethyl)-4,5α-epoxy-6α-hydroxy-3,7,7-trimethoxy-8-oxa-6,14-endoethanomorphinan was produced when 17-(cyclopropylmethyl)-4,5α-epoxy-3-m...

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Veröffentlicht in:Organic letters 2006-02, Vol.8 (3), p.523-526
Hauptverfasser: Watanabe, Akio, Kai, Toshitsugu, Nagase, Hiroshi
Format: Artikel
Sprache:eng
Schlagworte:
Esters
Magnetic Resonance Spectroscopy
Molecular Structure
Morphinans - chemical synthesis
Morphinans - chemistry
Stereoisomerism
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Zusammenfassung:A method was found for the novel synthesis of ortho ester derivatives that are potentially useful as selective ε opioid receptor ligands. An unexpected 17-(cyclopropylmethyl)-4,5α-epoxy-6α-hydroxy-3,7,7-trimethoxy-8-oxa-6,14-endoethanomorphinan was produced when 17-(cyclopropylmethyl)-4,5α-epoxy-3-methoxy-6α,14-dihydroxy-6β-(1,3-dithia-2-yl)-morphinan was treated in methanol with trimethyl orthoformate and CuO/CuCl2. This ortho ester derivative was then converted to an ester with acid. The structure of the ortho ester was determined by 2D NMR (HMBC) and mass spectra.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052883a