Literature DB >> 21516192

Synthetic Studies on the Ambiguine Family of Alkaloids: Construction of the ABCD Ring System.

Ryan J Rafferty1, Robert M Williams.   

Abstract

A racemic synthesis of the ABCD ring core of the ambiguines that preserves the tertiary alcohol has been accomplished in convergent synthesis in 10 synthetic steps, in an overall yield of 46% from commercially available 4-bromoindole and m-methylanisole.

Entities:  

Year:  2011        PMID： 21516192      PMCID： PMC3079252          DOI： 10.1016/j.tetlet.2010.09.086

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  8 in total

1.  The total synthesis of (+)-hapalindole Q by an organomediated Diels-Alder reaction.

Authors:  Aaron C Kinsman; Michael A Kerr
Journal:  J Am Chem Soc       Date:  2003-11-19       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.  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 marine natural products without using protecting groups.

Authors:  Phil S Baran; Thomas J Maimone; Jeremy M Richter
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

6.  Antimicrobial ambiguines from the cyanobacterium Fischerella sp. collected in Israel.

Authors:  Avi Raveh; Shmuel Carmeli
Journal:  J Nat Prod       Date:  2007-02       Impact factor: 4.050

7.  Synthesis of the bicyclic welwitindolinone core via an alkylation/cyclization cascade reaction.

Authors:  John A Brailsford; Ryan Lauchli; Kenneth J Shea
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

8.  Concise synthesis of the bicyclic scaffold of N-methylwelwitindolinone C isothiocyanate via an indolyne cyclization.

Authors:  Xia Tian; Alexander D Huters; Colin J Douglas; Neil K Garg
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005
  8 in total
  6 in total

1.  Total synthesis of hapalindoles J and U.

Authors:  Ryan J Rafferty; Robert M Williams
Journal:  J Org Chem       Date:  2011-12-09       Impact factor: 4.354

2.  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

3.  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

4.  FORMAL SYNTHESIS OF HAPALINDOLE O AND SYNTHETIC EFFORTS TOWARDS HAPALINDOLE K AND AMBIGUINE A.

Authors:  Ryan J Rafferty; Robert M Williams
Journal:  Heterocycles       Date:  2012-05-01       Impact factor: 0.831

5.  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

6.  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
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.