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Related Experiment Videos

Total Synthesis of (-)-Morphine.

Hirotatsu Umihara1, Satoshi Yokoshima2, Masayuki Inoue1

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

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 6, 2017
PubMed
Summary

The total synthesis of (-)-morphine was achieved in 18 steps. This novel approach utilized acid-mediated cyclization and singlet oxygen reactions for efficient morphinan skeleton construction.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • (-)-Morphine is a key opioid analgesic with a complex pentacyclic structure.
  • Efficient and stereoselective total synthesis of (-)-morphine remains a significant challenge in organic chemistry.

Purpose of the Study:

  • To achieve the first asymmetric total synthesis of (-)-morphine.
  • To develop a novel synthetic route amenable to late-stage diversification.

Main Methods:

  • The synthesis commenced from commercially available 7-methoxy-2-tetralone.
  • Key steps included acid-mediated E-ring cyclization and singlet oxygen-mediated C-ring manipulation.
  • The morphinan skeleton was assembled via 1,6-addition of an in situ generated secondary amine.

Main Results:

Keywords:
aldol reactionconjugate additionmorphinesinglet oxygentotal synthesis

Related Experiment Videos

  • An 18-step asymmetric total synthesis of (-)-morphine was successfully accomplished.
  • The synthesis demonstrated high stereocontrol throughout the sequence.
  • The route provides a viable pathway to the morphinan core structure.

Conclusions:

  • The developed synthetic strategy offers an efficient route to (-)-morphine.
  • This methodology can be adapted for the synthesis of morphine analogs.
  • The study advances the field of complex natural product synthesis.