Literature DB >> 19624126

Regiospecific and stereoselective syntheses of (+/-) morphine, codeine, and thebaine via a highly stereocontrolled intramolecular 4 + 2 cycloaddition leading to a phenanthrofuran system.

Gilbert Stork1, Ayako Yamashita, Julian Adams, Gary R Schulte, Richard Chesworth, Yoji Miyazaki, Jay J Farmer.   

Abstract

Total syntheses of the morphine alkaloids are described that use a direct stereoselective formation of the phenanthrofuran system via an intramolecular 4 + 2 cycloaddition of a diene tethered to the 4-position of a 7-methoxybenzofuran-3-carboxylic acid ester.

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Year:  2009        PMID： 19624126     DOI： 10.1021/ja9038505

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  7 in total

Review 1.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

Review 2.  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

3.  A Cascade Strategy Enables a Total Synthesis of (±)-Morphine.

Authors:  Shuyu Chu; Niels Münster; Tudor Balan; Martin D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-13       Impact factor: 15.336

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.  Asymmetric synthesis of (-)-naltrexone.

Authors:  Sun Dongbang; Blaine Pedersen; Jonathan A Ellman
Journal:  Chem Sci       Date:  2018-10-23       Impact factor: 9.825

Review 6.  Towards a molecular understanding of the biosynthesis of amaryllidaceae alkaloids in support of their expanding medical use.

Authors:  Adam M Takos; Fred Rook
Journal:  Int J Mol Sci       Date:  2013-05-31       Impact factor: 5.923

7.  Transition-metal-free C(sp3)-H/C(sp3)-H dehydrogenative coupling of saturated heterocycles with N-benzyl imines.

Authors:  Zhengfen Liu; Minyan Li; Guogang Deng; Wanshi Wei; Ping Feng; Quanxing Zi; Tiantian Li; Hongbin Zhang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2020-03-31       Impact factor: 9.825
  7 in total

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