The Enantioselective Synthesis of Morphine

Taber, Douglass F.; Neubert, Timothy D.; Schlecht, Matthew F.

doi:10.1002/chin.200546256

Cited by 4 publications

(6 citation statements)

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“…Nevertheless, opioid receptors do not exist in peripheral nerve so opiates do not have an effective clinical role in peripheral nerve blockade. Taking drugs in these classes also affect how the brain feels pleasure, in other words addictive [21,[90][91][92][93][94].…”

Section: Opiatesmentioning

confidence: 99%

“…For example, the drugs Levorphan and Dextrorphan are both mirror images of one another with quite similar structure to morphine. Levorphan, the left-handed molecule like naturally left-handed morphine, is several times more potent than morphine and is strongly addictive, while Dextrorphan, the right-handed molecule, has no analgesic ability and is also nonaddictive [21,[90][91][92][93][94].…”

Section: Opiatesmentioning

confidence: 99%

“…Morphine produces relaxation and sedation by depressing the nervous system [91,93,95]. Hydromorphone is synthesized from morphine that is much stronger than morphine but has less side effects and a lower dependency rate.…”

Section: Morphinementioning

confidence: 99%

“…Acetylation makes heroin more soluble in nonpolar solvents (i.e., oils and fats) and provides rapid pass through the blood-brain barrier which makes heroin much more potent than morphine because heroin is converted back to morphine in the brain. Patients with heroin addiction should seek advice from healthcare providers [91,93,95].…”

Section: Heroinmentioning

confidence: 99%

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The Local Anesthetic and Pain Relief Activity of Alkaloids

Sayhan¹,

Beyaz²,

Çeliktaş³

2017

Alkaloids - Alternatives in Synthesis, Modification and Application

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Alkaloids have been known for several centuries and have been mainly obtained from natural sources that presented important properties with biochemical, pharmacological, and medical effects in living organisms. Alkaloids are derived from amino acids like other important molecules in the functioning of life in our body. Hence, alkaloids are considered as pharmacologically important. Alkaloids are secondary metabolites widely distributed in leaves, stem, root, and fruits of plants which synthesize them. However, administration and consumption of them at right doses are beneficial in terms of health; excess doses will be definitely poisonous and may cause even death. The pharmacological activities of alkaloids are quite diverse. They are important natural products with a wide range of medicinal properties including relief of pain (e.g.

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Section: Opiatesmentioning

confidence: 99%

Section: Opiatesmentioning

confidence: 99%

Section: Morphinementioning

confidence: 99%

Section: Heroinmentioning

confidence: 99%

See 2 more Smart Citations

The Local Anesthetic and Pain Relief Activity of Alkaloids

Sayhan¹,

Beyaz²,

Çeliktaş³

2017

Alkaloids - Alternatives in Synthesis, Modification and Application

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“…Recently, thebaine and oripavine have become available from genetically modified poppies that produce much higher percentages of these alkaloids [17,18,19,20], now supplied by Tasmanian Alkaloids, Inc. [21]. Since the milestone synthesis of morphine by Gates [22] in 1952, there have been more than 30 total syntheses of morphine and related alkaloids and the academic pursuit continues unabated [23,24,25,26,27]. None of the reported syntheses are practical, however, for an industrial scale production.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone from Phenethyl Acetate

2019

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The total synthesis of (+)-10-keto-oxycodone was attained from phenethyl acetate in a stereoselective manner. Absolute stereochemistry was established via enzymatic dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) that furnished the corresponding cis-cyclohexadienediol whose configuration corresponds to the absolute stereochemistry of the ring C of (+)-10-keto-oxycodone. Intramolecular Heck reaction was utilized to establish the quaternary carbon at C-13, along with the dibenzodihydrofuran functionality. The C-14 hydroxyl and C-10 ketone were installed via SmI2-mediated radical cyclization, and oxidation of a benzylic alcohol (obtained from an intermediate nitrate azide), respectively. The synthesis of (+)-10-keto-oxycodone was completed in a total of 14 operations (21 steps) and an overall yield of ~2%. Experimental and spectral data are provided for key intermediates and new compounds.

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Chemistry of Opioids

Nagase¹

2011

Topics in Current Chemistry

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The Enantioselective Synthesis of Morphine

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 4 publications

References 1 publication

The Local Anesthetic and Pain Relief Activity of Alkaloids

The Local Anesthetic and Pain Relief Activity of Alkaloids

Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone from Phenethyl Acetate

Chemistry of Opioids

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