Literature DB >> 23020147

Synthesis of the pentacyclic skeleton of the indole alkaloid arboflorine.

Raul A Leal1, Danial R Beaudry, Saeed K Alzghari, Richmond Sarpong.   

Abstract

An effective synthesis of the pentacyclic core of the unusual Kopsia alkaloid arboflorine is reported. The success of the synthetic route rested on the use of a borylative C-H functionalization reaction, a convergent Suzuki cross-coupling to a C(2) halogenated indole, and an unprecedented transannular dehydrogenative C-N bond forming reaction.

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Year:  2012        PMID： 23020147      PMCID： PMC3481541          DOI： 10.1021/ol302535r

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


  14 in total

1.  Biologically active indole alkaloids from Kopsia arborea.

Authors:  Kuan-Hon Lim; Osamu Hiraku; Kanki Komiyama; Takashi Koyano; Masahiko Hayashi; Toh-Seok Kam
Journal:  J Nat Prod       Date:  2007-08-01       Impact factor: 4.050

2.  Pd(II)-catalyzed amination of C-H bonds using single-electron or two-electron oxidants.

Authors:  Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

3.  C-H activation for the construction of C-B bonds.

Authors:  Ibraheem A I Mkhalid; Jonathan H Barnard; Todd B Marder; Jaclyn M Murphy; John F Hartwig
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

4.  Methoxypyridines in the synthesis of Lycopodium alkaloids: total synthesis of (+/-)-lycoposerramine R.

Authors:  Vishnumaya Bisai; Richmond Sarpong
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

5.  Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors:  Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal:  Science       Date:  2001-11-22       Impact factor: 47.728

6.  Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.

Authors:  Tatsuo Ishiyama; Jun Takagi; Kousaku Ishida; Norio Miyaura; Natia R Anastasi; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-01-23       Impact factor: 15.419

7.  Arboflorine, an unusual pentacyclic monoterpenoid indole alkaloid incorporating a third nitrogen atom.

Authors:  Kuan-Hon Lim; Toh-Seok Kam
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

8.  Total synthesis of (+)-lyconadin A and related compounds via oxidative C-N bond formation.

Authors:  Scott P West; Alakesh Bisai; Andrew D Lim; Raja R Narayan; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

9.  Domino Heck-aza-Michael reactions: efficient access to 1-substituted tetrahydro-beta-carbolines.

Authors:  Daniel L Priebbenow; Luke C Henderson; Frederick M Pfeffer; Scott G Stewart
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

10.  An efficient total synthesis of (-)-huperzine A.

Authors:  Rui Ding; Bing-Feng Sun; Guo-Qiang Lin
Journal:  Org Lett       Date:  2012-08-17       Impact factor: 6.005
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  3 in total

1.  Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones.

Authors:  Bram B C Peters; Jira Jongcharoenkamol; Suppachai Krajangsri; Pher G Andersson
Journal:  Org Lett       Date:  2020-12-22       Impact factor: 6.005

2.  Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors.

Authors:  A John Blacker; Katherine E Jolley
Journal:  Beilstein J Org Chem       Date:  2015-12-02       Impact factor: 2.883

Review 3.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823
  3 in total

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