Literature DB >> 20929213

Asymmetric total synthesis of ent-cyclooroidin.

Sabuj Mukherjee1, Rasapalli Sivappa, Muhammed Yousufuddin, Carl J Lovely.   

Abstract

An enantiospecific total synthesis of the pyrrole-imidazole natural product cyclooroidin from histidine is described. The key N1-C9 bond is constructed through an intramolecular SN2-type of reaction of a chloro ester. Subsequent imidazole azidation at the 2-position, pyrrole bromination, azide reduction, and deprotection leads to the completion of the synthesis.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20929213      PMCID： PMC3099645          DOI： 10.1021/ol1020916

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


  18 in total

1.  Agelastatin E, agelastatin F, and benzosceptrin C from the marine sponge Agelas dendromorpha.

Authors:  Supriya Tilvi; Céline Moriou; Marie-Thérèse Martin; Jean-François Gallard; Jonathan Sorres; Kirti Patel; Sylvain Petek; Cécile Debitus; Ludmila Ermolenko; Ali Al-Mourabit
Journal:  J Nat Prod       Date:  2010-04-23       Impact factor: 4.050

2.  Agelastatins C and D, new pentacyclic bromopyrroles from the sponge Cymbastela sp., and potent arthropod toxicity of (-)-agelastatin A.

Authors:  T W Hong; D R Jímenez; T F Molinski
Journal:  J Nat Prod       Date:  1998-01       Impact factor: 4.050

3.  The alpha-hydrazino analog of histidine.

Authors:  M Sletzinger; R A Firestone; D F Reinhold; C S Rooney; W H Nicholson
Journal:  J Med Chem       Date:  1968-03       Impact factor: 7.446

4.  Total synthesis of all (-)-Agelastatin alkaloids.

Authors:  Mohammad Movassaghi; Dustin S Siegel; Sunkyu Han
Journal:  Chem Sci       Date:  2010-01-01       Impact factor: 9.825

5.  Nagelamides Q and R, novel dimeric bromopyrrole alkaloids from sponges Agelas sp.

Authors:  Atsushi Araki; Takaaki Kubota; Kazuki Aoyama; Yuzuru Mikami; Jane Fromont; Jun'ichi Kobayashi
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

6.  Total synthesis of the putative structure of nagelamide D.

Authors:  Manojkumar R Bhandari; Rasapalli Sivappa; Carl J Lovely
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

7.  Asymmetric annulation toward pyrrolopiperazinones: concise enantioselective syntheses of pyrrole alkaloid natural products.

Authors:  Barry M Trost; Guangbin Dong
Journal:  Org Lett       Date:  2007-05-12       Impact factor: 6.005

8.  Synthesis of 7-(15)N-Oroidin and evaluation of utility for biosynthetic studies of pyrrole-imidazole alkaloids by microscale (1)H-(15)N HSQC and FTMS.

Authors:  Yong-Gang Wang; Brandon I Morinaka; Jeremy Chris P Reyes; Jeremy J Wolff; Daniel Romo; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

9.  Benzosceptrins A and B with a unique benzocyclobutane skeleton and nagelamide S and T from Pacific sponges.

Authors:  Jérôme Appenzeller; Supriya Tilvi; Marie-Thérèse Martin; Jean-François Gallard; Hoda El-bitar; Elise Tran Huu Dau; Cécile Debitus; Dominique Laurent; Céline Moriou; Ali Al-Mourabit
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

10.  Massadine, a novel geranylgeranyltransferase type I inhibitor from the marine sponge Stylissa aff. massa.

Authors:  Shinichi Nishimura; Shigeki Matsunaga; Mitsuyoshi Shibazaki; Kenichi Suzuki; Kazuo Furihata; Rob W M van Soest; Nobuhiro Fusetani
Journal:  Org Lett       Date:  2003-06-26       Impact factor: 6.005
View more
  8 in total

1.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

2.  Thio acid-mediated conversion of azides to amides - exploratory studies en route to oroidin alkaloids.

Authors:  Apsara K Herath; Manoj R Bhandari; Delphine Gout; Muhammed Yousufuddin; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2017-08-24       Impact factor: 2.415

Review 3.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors:  Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal:  Nat Prod Rep       Date:  2011-05-09       Impact factor: 13.423

4.  Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.

Authors:  Manojkumar R Bhandari; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2011-02-21       Impact factor: 6.005

5.  Synthesis of 2-imidazolones and 2-iminoimidazoles.

Authors:  Heather M Lima; Carl J Lovely
Journal:  Org Lett       Date:  2011-10-12       Impact factor: 6.005

Review 6.  Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

Authors:  Xiao Wang; Zhiqiang Ma; Xiaolei Wang; Saptarshi De; Yuyong Ma; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2014-05-15       Impact factor: 6.222

7.  NHC-Cu-catalyzed addition of propargylboron reagents to phosphinoylimines. Enantioselective synthesis of trimethylsilyl-substituted homoallenylamides and application to the synthesis of S-(-)-cyclooroidin.

Authors:  Nicholas W Mszar; Fredrik Haeffner; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-02-20       Impact factor: 15.419

8.  Efficient Total Synthesis of Lissodendrin B, 2-Aminoimidazole Marine Alkaloids Isolated from Lissodendoryx (Acanthodoryx) Fibrosa.

Authors:  Xianfeng Wei; Xuelong Hu; Rilei Yu; Shengbiao Wan; Tao Jiang
Journal:  Mar Drugs       Date:  2019-12-31       Impact factor: 5.118
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.