Formal Total Synthesis of (—)‐Morphine by Cuprate Conjugate Addition

1996/12/01 by Johann Mulzer, Gerd Dürner, Dirk Trauner · 4 citations
Chemistry · Mathematics · Medicine · Pharmacology, Toxicology and Pharmaceutics · #Alkaloids: synthesis and pharmacology #Anesthesia #Chemical synthesis and alkaloids #Chemistry #Chromatography in Natural Products #Conjugate #Cuprate #Enone #Materials science #Mathematics #Medicine #Morphine #Stereochemistry #Steric effects #Total synthesis

paper · doi:10.1002/anie.199628301

openalex publication_date 1996/12/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29

Abstract

Conjugate addition of a vinyl cuprate to the sterically and electronically very demanding enone 1 is the key step of a short asymmetric total synthesis of (—)-dihydro-codeinone (2), an immediate precursor of (-)-morphine.

Citations

• Asymmetric synthesis of either enantiomer of opium alkaloids and morphinans. Total synthesis of (-)- and (+)-dihydrocodeinone and (-)- and (+)-morphine
• Synthetic opium alkaloids and derivatives. A short total synthesis of (.+-.)-dihydrothebainone, (.+-.)-dihydrocodeinone, and (.+-.)-nordihydrocodeinone as an approach to a practical synthesis of morphine, codeine, and congeners
• Convergent synthesis of (.+-.)-dihydroisocodeine in 11 steps by the tandem radical cyclization strategy. A formal total synthesis of (.+-.)-morphine
• Studies culminating in the total synthesis of (dl)-morphine

Cited by

• Regiospecific and Stereoselective Syntheses of (±) Morphine, Codeine, and Thebaine via a Highly Stereocontrolled Intramolecular 4 + 2 Cycloaddition Leading to a Phenanthrofuran System
• Asymmetric Total Synthesis of (+)-Codeine via Intramolecular Carbenoid Insertion
• Divergent Enantioselective Synthesis of (−)-Galanthamine and (−)-Morphine
• Morphine [wikipedia]