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Total synthesis of (-)-morphine.

Hifumi Koizumi1, Satoshi Yokoshima, Tohru Fukuyama

  • 1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

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Researchers achieved an efficient total synthesis of (-)-morphine, a complex opioid alkaloid. This 17-step synthesis utilizes key reactions like enzymatic resolution and Suzuki-Miyaura coupling for constructing the morphinan core.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • (-)-Morphine is a crucial opiate alkaloid with significant analgesic properties.
  • Existing synthetic routes to morphine are often lengthy and inefficient.
  • Developing novel synthetic strategies is vital for accessing morphine analogs and understanding its structure-activity relationships.

Purpose of the Study:

  • To establish an efficient and scalable total synthesis of (-)-morphine.
  • To explore novel synthetic methodologies for constructing the complex morphinan core.
  • To provide a reliable route for the preparation of morphine and its derivatives.

Main Methods:

  • Enzymatic resolution and Suzuki-Miyaura coupling for cyclohexenol unit preparation.
  • Intramolecular aldol reaction and intramolecular 1,6-addition for morphinan core construction.
  • Mild deprotection using 2,4-dinitrobenzenesulfonyl (DNs) group for facile skeleton formation.

Main Results:

  • An efficient total synthesis of (-)-morphine was achieved in 5% overall yield.
  • The longest linear sequence comprised 17 steps, starting from 2-cyclohexen-1-one.
  • A novel synthetic route to a cyclohexenol unit with an N-methyl-DNs-amide moiety was established.

Conclusions:

  • The developed synthetic route is efficient for producing (-)-morphine.
  • The key steps employed offer a versatile approach to the morphinan skeleton.
  • This synthesis provides a valuable platform for further exploration of opioid chemistry.