ChemInform Abstract: Tetra‐ and Hexahydrodibenzofuran Morphine‐Like Derivatives.

Labidalle, Serge; Zhang, Y. M.; Moskowitz, H.; Thal, C.; Miocque, M.; Degryse, M.; Fortin, M.; Delevallee, F.

doi:10.1002/chin.198951292

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“…A different, and very rarely explored, modification is based on the cleavage of rings D and E, which leads to hydrodibenzofurans that are structurally similar to Pummerer's ketone ( 36 ). This class of compound is represented by 37 , which showed selectivity for μ and κ receptors in binding assays …”

Section: Discussionmentioning

confidence: 99%

The [4 + 2] Addition of Singlet Oxygen to Thebaine: New Access to Highly Functionalized Morphine Derivatives via Opioid Endoperoxides

2000

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The photooxidation of thebaine (3) with a sun lamp affords two main products: hydrodibenzofuran 10 (major) and benzofuran 11 (minor). The latter compound becomes predominant if a Hg lamp is used instead of a sun lamp. The formation of 10 proceeds via an endoperoxide intermediate that undergoes oxidation at the nitrogen atom. Protection of the nitrogen either by protonation or quaternization prevents its oxidation and thus the photooxidation of 3 in acid media constitutes a one-pot procedure for the preparation of 14-hydroxycodeinone 35. Photooxidation of the thebaine ammonium salt 31 allows the isolation in good yields of the corresponding to thebaine endoperoxide 32. The selective protection and reduction of the keto, aldehyde, and olefinic groups of hydrodibenzofuran 10 allowed the preparation of several diol and keto alcohol derivatives. This is the first report on the use of photooxidation to functionalize thebaine at C(6) and C(14) and also the first on the isolation of opioid endoperoxides.

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Section: Discussionmentioning

confidence: 99%

The [4 + 2] Addition of Singlet Oxygen to Thebaine: New Access to Highly Functionalized Morphine Derivatives via Opioid Endoperoxides

2000

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ChemInform Abstract: Tetra‐ and Hexahydrodibenzofuran Morphine‐Like Derivatives.

Abstract: ChemInform Abstract The morphine analogues (I)-(III) are prepared by means of previously described methodologies. Some of these derivatives have a high affinity vs. µ opiate receptors and also display activity in the hot plate test.

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The [4 + 2] Addition of Singlet Oxygen to Thebaine: New Access to Highly Functionalized Morphine Derivatives via Opioid Endoperoxides

The [4 + 2] Addition of Singlet Oxygen to Thebaine: New Access to Highly Functionalized Morphine Derivatives via Opioid Endoperoxides

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