Chapter 1 The Morphine Alkaloids

Bentley, K. W.

doi:10.1016/s1876-0813(08)60306-1

Cited by 5 publications

(5 citation statements)

References 195 publications

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“…Synthesis (Kraufc (E. Merck), 1925, Juby et al, 1968, Ehrhart and Ruschig 1972: Thebaine is oxidized with hydrogene peroxide to 14-hydroxycodeinone (Bentley 1954, Hauser 1974, which is hydrogenated directly or via its oxime, or its bromination products to oxycodone. The reduction of 14-hydroxycodeinone can also be carried out with sodium hydrosulfite.…”

Section: Oxycodonementioning

confidence: 99%

Opioids: 3.4 Opioids with Clinical Relevance

Friderichs

Buschmann

2002

Analgesics

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Section: Oxycodonementioning

confidence: 99%

Opioids: 3.4 Opioids with Clinical Relevance

Friderichs

Buschmann

2002

Analgesics

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“…The hasubanan alkaloids are a family of over 70 botanical metabolites. − The namesake member, (−)-hasubanonine ( 19 ), was first isolated from Stephania japonica in 1951; − these alkaloids possess a variety of biological properties, including antimicrobial, antiviral (hepatitis B), and opioid receptor binding activities . The acutumine alkaloids are a smaller family, with 15 members currently known .…”

Section: Introductionmentioning

confidence: 99%

Substrate-Modified Functional Group Reactivity: Hasubanan and Acutumine Alkaloid Syntheses

King

Herzon

2014

J. Org. Chem.

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Functional group taxonomy provides a powerful conceptual framework to classify and predict the chemical reactivity of molecular structures. These principals are most effective in monofunctional settings, wherein individual functional groups can be analyzed without complications. In more complex settings, the predictive value of these analyses decreases as alternative reaction pathways, promoted by neighboring substituents and aggregate molecular properties, emerge. We refer to this phenomenon as substrate-modified functional group reactivity. In this Perspective, we explain how substrate-modified functional group reactivity molded our synthetic routes to the hasubanan and acutumine alkaloids. These investigations underscore the potential for discovery and insight that can only be gained by studying the reactivity of complex multifunctional structures.

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“…Previous attempts [5][6][7] at this conversion have been unsuccessful, due to the sensitivity of the allylic and dienol ether functions to acids, bases, and nucleophiles. 8,9 We now wish to disclose that this transformation can be accomplished conveniently by the use of L-Selectride (Aldrich).…”

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confidence: 99%

“…12 The ease of this transformation allowed investigation of the chemistry of oripavine for the first time. 8 In order to demonstrate its potential use in opioid synthesis, it was necessary to compare the chemistry with that of thebaine. The two most important reactions of thebaine are the oxidation to 14-hydroxycodeinone, leading to the opiate antagonists, and the Diels-Alder reactions leading to the orvinols, a class of very potent and important opioid drugs.…”

mentioning

confidence: 99%