Rhazinilam Synthesis Essay

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  • Heteroaromatic Synthesis: The Tokuyama Synthesis of (-)-Rhazinilam

    Mei-Huey Lin of the National Changhua University of Education rearranged (J. Org. Chem.2014, 79, 2751. ) the initial allene derived from 1 to the γ-chloroenone. Displacement with acetate followed by hydrolysis led to the furan 2. A. Stephen K. Hashmi of Ruprecht-Karls-Universität Heidelberg showed (Angew. Chem. Int. Ed.2014, 53, 3715. ) that the Au-catalyzed conversion of the bis alkyne 3 proceeded selectively to give 5.

    Tehshik P. Yoon of the University of Wisconsin used (Angew. Chem. Int. Ed.2014, 53, 793. ) visible light with a Ru catalyst to rearrange the azide 6 to the pyrrole 7. Cheol-Min Park, now at UNIST, found (Chem. Sci.2014, 5, 2347. ) that a Ni catalyst reorganized the methoxime 8 to the pyrrole 9. A Rh catalyst converted 8 to the corresponding pyridine (not illustrated).

    In the course of a synthesis of opioid ligands, Kenner C. Rice of the National Institute of Drug Abuse optimized (J. Org. Chem.2014, 79, 5007. ) the preparation of the pyridine 11 from the alcohol 10. Vincent Tognetti and Cyrille Sabot of the University of Rouen heated (J. Org. Chem.2014, 79, 1303. ) 12 and 13 under microwave irradiation to give the 3-hydroxy pyridine 14.

    Tomislav Rovis of Colorado State University prepared (J. Am. Chem. Soc.2014, 136, 2735. ) the pyridine 17 by the Rh-catalyzed combination of 15 with 16. Fabien Gagosz of the Ecole Polytechnique rearranged (Angew. Chem. Int. Ed.2014, 53, 4959. ) the azirine 18, readily available from the oxime of the β-keto ester, to the pyridine 19.

    Matthias Beller of the Universität Rostock used (Chem. Eur. J.2014, 20, 1818. ) a Zn catalyst to mediate the opening of the epoxide 21 with the aniline 20. A Rh catalyst effected the oxidation and cylization of the product amino alcohol to the indole 22. Sreenivas Katukojvala of the Indian Institute of Science Education & Research showed (Angew. Chem. Int. Ed.2014, 53, 4076. ) that the diazo ketone 23 could be used to anneal a benzene ring onto the pyrrole 24, leading to the 2,7-disubstituted indole 25. Tomoya Miura and Masahiro Murakami of Kyoto University developed (J. Am. Chem. Soc.2014, 136, 2272. ) the one-pot Cu-catalyzed dipolar cycloaddition of tosyl azide to the alkyne of 26, followed by Rh-mediated intramolecular addition to the benzene ring. That product could be oxidized directly to the indole 27. Edward A. Anderson of the University of Oxford observed (Chem. Commun.2014, 50, 5187. ) that the sulfonamide 29, from Pd-catalyzed cyclization of 28, could also be desulfonylated and oxidized to the indole.

    (-)-Rhazinilam (32), isolated from Rhazya stricta Decaisne, interferes with tubulin polymerization and dynamics. To assemble 32, Hidetoshi Tokuyama of Tohoku University devised (Angew. Chem. Int. Ed.2013, 52, 7168. ) the intramolecular cyclization of 30 to give the pyrrole 31.

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