Literature DB >> 28378531

Total Synthesis of (-)-Morphine.

Hirotatsu Umihara1, Satoshi Yokoshima2, Masayuki Inoue1, Tohru Fukuyama2.   

Abstract

Asymmetric total synthesis of (-)-morphine has been accomplished in 18 steps from commercially available 7-methoxy-2-tetralone. Our synthesis features a simple transformation from a readily prepared chiral intermediate, construction of the E-ring by acid-mediated cyclization, and singlet oxygen-mediated manipulation of the C-ring. Transformation of the final stage involves construction of the morphinan skeleton by means of 1,6-addition of in situ generated secondary amine.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aldol reaction; conjugate addition; morphine; singlet oxygen; total synthesis

Mesh:

Substances:

Year:  2017        PMID: 28378531     DOI: 10.1002/chem.201701438

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  5 in total

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Authors:  Nina Hartrampf; Nils Winter; Gabriele Pupo; Brian M Stoltz; Dirk Trauner
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Review 2.  Interpol review of controlled substances 2016-2019.

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Review 3.  The DARK Side of Total Synthesis: Strategies and Tactics in Psychoactive Drug Production.

Authors:  Schuyler A Chambers; Jenna M DeSousa; Eric D Huseman; Steven D Townsend
Journal:  ACS Chem Neurosci       Date:  2018-02-01       Impact factor: 4.418

4.  Programmed serial stereochemical relay and its application in the synthesis of morphinans.

Authors:  Kun Ho Kenny Park; Rui Chen; David Y-K Chen
Journal:  Chem Sci       Date:  2017-08-30       Impact factor: 9.825

5.  Multienzyme One-Pot Cascades Incorporating Methyltransferases for the Strategic Diversification of Tetrahydroisoquinoline Alkaloids.

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Journal:  Angew Chem Int Ed Engl       Date:  2021-07-16       Impact factor: 16.823

  5 in total

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