Synthesis of a Morphinan Derivative by Oxidative Ring Closure

Franck, Burchard; Dunkelmann, G.; Lubs, H. J.

doi:10.1002/anie.196710751

Cited by 34 publications

(6 citation statements)

References 6 publications

(4 reference statements)

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“…1982, 47, 3270. (5) Rao, Y. S.; Filler, R. Synthesis 1975, 749 and references cited herein. (6) Meyers, A. I. "Heterocycles in Organic Synthesis"; Wiley: New York, 1974; Vol.…”

Section: Methodsmentioning

confidence: 99%

Action of diazomethane on (Z/E)-2-methyl(or phenyl)-4-benzylidene-5(4H)-oxazolones

Cativiela¹,

Dı́az-de-Villegas²,

Mayoral³

et al. 1984

J. Org. Chem.

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We have been interested in the synthesis of (Z/E)-2methyl(or phenyl)-4-(a-arylethylidene)-5(4fl)-oxazolones 5 and 6 for several years. Although earlier authors1 found that acetophenones and hippuric acid could not condense under Plóchl-Erlenmeyer conditions, 2-phenyl derivatives were prepared2 with moderate or low yields in acetic anhydride and lead acetate as isomeric mixtures with the Z isomer predominating. The pure isomers were obtained by crystallization or by suitable isomerization procedures. Attempts to prepare 2-methyl derivatives have been unsuccessful. On the other hand several workers3 have inti) Rao, Y. S.

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“…1982, 47, 3270. (5) Rao, Y. S.; Filler, R. Synthesis 1975, 749 and references cited herein. (6) Meyers, A. I. "Heterocycles in Organic Synthesis"; Wiley: New York, 1974; Vol.…”

Section: Methodsmentioning

confidence: 99%

Action of diazomethane on (Z/E)-2-methyl(or phenyl)-4-benzylidene-5(4H)-oxazolones

Cativiela¹,

Dı́az-de-Villegas²,

Mayoral³

et al. 1984

J. Org. Chem.

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“…Much of this attention has been focused on the transformation into morphinandienonetype alkaloids. [138][139][140][141][142][143][144][145][146] In the early studies, the biomimetic phenolic coupling reaction using chemical oxidants or some other synthetic methods such as the Pschorr reaction, photochemical coupling reaction, or benzyne reaction, were continually employed. Despite large efforts, the yields of the coupling step were usually low and, in general, these methodologies did not afford practical routes to morphinandienone alkaloids.…”

Section: Efficient Synthesis Of Morphinandienone Alkaloidmentioning

confidence: 99%

Development and Application of New Oxidation Systems Utilizing Oxometalate Catalysts

Hamamoto

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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This review describes our recent efforts in the development and application of new oxidation systems utilizing oxometalate catalysts. The novel use of heteropoly acid (HPA), an acidic oxometalate catalyst, in hypervalent iodine-mediated oxidations provided an effective strategy to generate cation radical species that enables a variety of direct C-H functionalizations of aromatic compounds. This strategy brought a facile biaryl synthesis and new spirodienone syntheses in aromatic oxidation chemistry. Moreover, this strategy opens up a facile synthetic route to morphinandienone alkaloids. On the other hand, the use of oxometalate catalyst together with poly(N-isopropylacrylamide) (PNIPAAm)-based polymer in the development of new solid-phase catalyst provided a novel reaction system in water. Due to the characteristic temperature-responsive intelligence of PNIPAAm, this reaction system brought a remarkable acceleration of the reactivity and ease of catalyst recovering in catalytic oxidation that uses hydrogen peroxide or oxygen gas (O 2 ) as primary oxidant. In addition, the recovered solid-phase catalyst could be used for consecutive reactions without any significant loss of its catalytic efficacy.

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“…C8‐2’ and C8‐6’ coupling leads to the generation of the aporphines corytuberine ( 5 ) and isoboldine ( 6 ), respectively. While these are still interesting alkaloids, they are undesirable dead ends in the intended construction of the morphinane scaffold [17–19] . Only salutaridine ( 7 , 4a–2′‐connectivity) can be further converted to morphine ( 1 a ) (Scheme 1B).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Morphinans through Anodic Aryl‐Aryl Coupling

Vierengel

Geske

Sato

et al. 2021

The Chemical Record

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The morphinans are an important class of structurally fascinating and physiologically important natural products as exemplified by the famous opium alkaloids of the morphine family. Although this class of secondary metabolites from the juice of the opium poppy capsule was already used for medicinal purposes thousands of years ago, chemical modifications are still being applied to the core structure today in order to achieve the most specific effect on the various receptor subtypes possible with the fewest possible side effects. The unusual architecture of the morphinan core has also proven to be a highly challenging target for total synthesis. This review highlights electrosynthetic approaches towards natural and semisynthetic morphinan alkaloids. The historical progress in applying anodic aryl‐aryl couplings to the construction of the morphinan framework is described in chronological order while particular benefits and challenges concerning the electrochemical transformations are grouped together, including the influence of substitution patterns, protecting groups, and reaction conditions.

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Synthesis of a Morphinan Derivative by Oxidative Ring Closure

Cited by 34 publications

References 6 publications

Action of diazomethane on (Z/E)-2-methyl(or phenyl)-4-benzylidene-5(4H)-oxazolones

Action of diazomethane on (Z/E)-2-methyl(or phenyl)-4-benzylidene-5(4H)-oxazolones

Development and Application of New Oxidation Systems Utilizing Oxometalate Catalysts

Synthesis of Morphinans through Anodic Aryl‐Aryl Coupling

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