Literature DB >> 17975918

Synthesis of the ABC- and D-ring systems of the indole alkaloid ambiguine G.

Aroop Chandra1, Rajesh Viswanathan, Jeffrey N Johnston.   

Abstract

A glycine Schiff base Michael addition is used in sequence with free radical-mediated aryl amination to ultimately arrive at the ambiguine G ABC-tricycle convergently. Additionally, thermal Diels-Alder cycloaddition of beta-chloromethacrolein with Cohen's diene is used to diastereoselectively construct the D-cyclohexane ring bearing a neopentyl chloride.

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Year:  2007        PMID： 17975918      PMCID： PMC2617716          DOI： 10.1021/ol702247a

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


  10 in total

1.  Total synthesis of (+/-)-hapalindole Q.

Authors:  A C Kinsman; M A Kerr
Journal:  Org Lett       Date:  2001-10-04       Impact factor: 6.005

2.  Nonconventional carbon additions to azomethines. aryl amination/indoline synthesis by direct aryl radical addition to azomethine nitrogen.

Authors:  J N Johnston; M A Plotkin; R Viswanathan; E N Prabhakaran
Journal:  Org Lett       Date:  2001-04-05       Impact factor: 6.005

3.  Isolation of a nitrile-containing indole alkaloid from the terrestrial blue-green alga hapalosiphon delicatulus

Authors: 
Journal:  J Nat Prod       Date:  1998-10       Impact factor: 4.050

4.  Rapid synthesis of the N-methylwelwitindolinone skeleton.

Authors:  James A MacKay; Raynauld L Bishop; Viresh H Rawal
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

5.  Total synthesis of (+/-)-welwitindolinone a isonitrile.

Authors:  Sarah E Reisman; Joseph M Ready; Atsushi Hasuoka; Catherine J Smith; John L Wood
Journal:  J Am Chem Soc       Date:  2006-02-08       Impact factor: 15.419

6.  Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G.

Authors:  Phil S Baran; Jeremy M Richter
Journal:  J Am Chem Soc       Date:  2005-11-09       Impact factor: 15.419

7.  Free radical-mediated vinyl amination: access to N,N-dialkyl enamines and their beta-stannyl and beta-thio derivatives.

Authors:  Erode N Prabhakaran; Benjamin M Nugent; Amie L Williams; Kristen E Nailor; Jeffrey N Johnston
Journal:  Org Lett       Date:  2002-11-28       Impact factor: 6.005

8.  Oxidation of silyl enol ethers by using IBX and IBX.N-oxide complexes: a mild and selective reaction for the synthesis of enones.

Authors:  K C Nicolaou; David L F Gray; Tamsyn Montagnon; Scott T Harrison
Journal:  Angew Chem Int Ed Engl       Date:  2002-03-15       Impact factor: 15.336

9.  Free radical-mediated aryl amination and its use in a convergent [3 + 2] strategy for enantioselective indoline alpha-amino acid synthesis.

Authors:  Rajesh Viswanathan; Erode N Prabhakaran; Michael A Plotkin; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2003-01-08       Impact factor: 15.419

10.  The first azacyclopentenyl carbinyl radical isomerizations (ACCRI): independent use of steric and electronic (polarization) effects as gating elements.

Authors:  Rajesh Viswanathan; Daniel Mutnick; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2003-06-18       Impact factor: 15.419
  10 in total
  10 in total

1.  Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach.

Authors:  Jeremy M Richter; Yoshihiro Ishihara; Takeshi Masuda; Brandon W Whitefield; Tomás Llamas; Antti Pohjakallio; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

2.  Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua.

Authors:  Shunyan Mo; Aleksej Krunic; George Chlipala; Jimmy Orjala
Journal:  J Nat Prod       Date:  2009-05-22       Impact factor: 4.050

3.  Total synthesis of the chlorine-containing hapalindoles K, A, and G.

Authors:  Aroop Chandra; Jeffrey N Johnston
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-07       Impact factor: 15.336

4.  Hapalindole-related alkaloids from the cultured cyanobacterium Fischerella ambigua.

Authors:  Shunyan Mo; Aleksej Krunic; Bernard D Santarsiero; Scott G Franzblau; Jimmy Orjala
Journal:  Phytochemistry       Date:  2010-10-19       Impact factor: 4.072

5.  Scalable Total Syntheses of (-)-Hapalindole U and (+)-Ambiguine H.

Authors:  Thomas J Maimone; Yoshihiro Ishihara; Phil S Baran
Journal:  Tetrahedron       Date:  2015-05-02       Impact factor: 2.457

6.  Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole Functionalizations.

Authors:  Rebecca E Johnson; Hwisoo Ree; Marco Hartmann; Laura Lang; Shota Sawano; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2019-02-04       Impact factor: 15.419

7.  Brain-penetrant tetrahydronaphthalene thromboxane A2-prostanoid (TP) receptor antagonists as prototype therapeutics for Alzheimer's disease.

Authors:  James H Soper; Shimpei Sugiyama; Katie Herbst-Robinson; Michael J James; Xiaozhao Wang; John Q Trojanowski; Amos B Smith; Virginia M-Y Lee; Carlo Ballatore; Kurt R Brunden
Journal:  ACS Chem Neurosci       Date:  2012-07-27       Impact factor: 4.418

8.  Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure.

Authors:  Yang Liu; Li-Jie Cheng; Hai-Tao Yue; Wen Che; Jian-Hua Xie; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2016-04-12       Impact factor: 9.825

9.  Free radical-mediated aryl amination: convergent two- and three-component couplings to chiral 2,3-disubstituted indolines.

Authors:  Rajesh Viswanathan; Colin R Smith; Erode N Prabhakaran; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2008-03-20       Impact factor: 4.198

10.  Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G.

Authors:  Lingbowei Hu; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2021-07-19       Impact factor: 15.419
  10 in total

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