Literature DB >> 18335949

Total synthesis of (+/-)-mersicarpine.

Jakob Magolan1, Cheryl A Carson, Michael A Kerr.   

Abstract

The first total synthesis of the indole alkaloid mersicarpine is reported. Key steps include a beta-dicarbonyl radical cyclization, as well as an oxidation of the benzopyrrole moiety to establish the masked 1,2-dicarbonyl functionality. An X-ray crystal structure and discussion of the 1H NMR behavior of the natural product are also presented.

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Year:  2008        PMID： 18335949     DOI： 10.1021/ol800259s

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

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Review 4.  Some aspects of radical cascade and relay reactions.

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Review 6.  Synthesis of indole derivatives as prevalent moieties present in selected alkaloids.

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8.  2-Hy-droxy-2-methyl-1-phenyl-indolin-3-one.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-09

9.  Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids from a common intermediate through regiocontrolled cyclizations by Staudinger reactions†Electronic supplementary information (ESI) available: Experimental details and procedures, compound characterization data, copies of 1H and 13C NMR spectra for new compounds. See DOI: 10.1039/c4qo00312hClick here for additional data file.

Authors:  Zining Li; Qian Geng; Zhe Lv; Beau P Pritchett; Katsuaki Baba; Yoshitaka Numajiri; Brian M Stoltz; Guangxin Liang
Journal:  Org Chem Front       Date:  2015-01-27       Impact factor: 5.281

10.  Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.

Authors:  Yang Yang; Yu Bai; Siyuan Sun; Mingji Dai
Journal:  Org Lett       Date:  2014-11-20       Impact factor: 6.005
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