Literature DB >> 22616754

Total synthesis of Akuammiline alkaloid (-)-vincorine via intramolecular oxidative coupling.

Weiwei Zi1, Weiqing Xie, Dawei Ma.   

Abstract

An asymmetric total synthesis of the Akuammiline alkaloid (-)-vincorine (18 steps from 5-methoxytryptamine, 5% overall yield) is described. The key steps include Pd-catalyzed direct C-H functionalization of indole derivatives, organocatalyzed asymmetric Michael addition of aldehydes to alkylidene malonates, and intramolecular oxidative coupling between indole and malonate moieties.

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Year:  2012        PMID： 22616754     DOI： 10.1021/ja303602f

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


  16 in total

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Authors:  Lingchao Cai; Kui Zhang; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2016-03-04       Impact factor: 15.419

2.  Use of a biosynthetic intermediate to explore the chemical diversity of pseudo-natural fungal polyketides.

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3.  Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  European J Org Chem       Date:  2014-06-01

4.  Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.

Authors:  Jie S Zhu; Jung-Ho Son; Andrew P Teuthorn; Makhluf J Haddadin; Mark J Kurth; Dean J Tantillo
Journal:  J Org Chem       Date:  2017-09-28       Impact factor: 4.354

5.  Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A.

Authors:  Jesus Moreno; Elias Picazo; Lucas A Morrill; Joel M Smith; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

6.  Intramolecular C(sp3)-N coupling by oxidation of benzylic C,N-dianions.

Authors:  Jenna L Jeffrey; Emily S Bartlett; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-16       Impact factor: 15.336

7.  Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

Authors:  Robert B Susick; Lucas A Morrill; Elias Picazo; Neil K Garg
Journal:  Synlett       Date:  2017       Impact factor: 2.454

8.  Nine-step enantioselective total synthesis of (-)-vincorine.

Authors:  Benjamin D Horning; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-04-19       Impact factor: 15.419

9.  Access to the akuammiline family of alkaloids: total synthesis of (+)-scholarisine A.

Authors:  Gregory L Adams; Patrick J Carroll; Amos B Smith
Journal:  J Am Chem Soc       Date:  2012-12-26       Impact factor: 15.419

10.  Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies.

Authors:  Elias Picazo; Lucas A Morrill; Robert B Susick; Jesus Moreno; Joel M Smith; Neil K Garg
Journal:  J Am Chem Soc       Date:  2018-05-15       Impact factor: 15.419
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