Literature DB >> 24151973

A diastereoselective oxa-Pictet-Spengler-based strategy for (+)-frenolicin B and epi-(+)-frenolicin B synthesis.

Yinan Zhang1, Xiachang Wang, Manjula Sunkara, Qing Ye, Larissa V Ponomereva, Qing-Bai She, Andrew J Morris, Jon S Thorson.   

Abstract

An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.

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Year:  2013        PMID： 24151973      PMCID： PMC3877857          DOI： 10.1021/ol4027649

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


  13 in total

Review 1.  Pyranonaphthoquinone antibiotics--isolation, structure and biological activity.

Authors:  M A Brimble; L J Duncalf; M R Nairn
Journal:  Nat Prod Rep       Date:  1999-06       Impact factor: 13.423

2.  Nonsteroidal selective glucocorticoid modulators: the effect of C-5 alkyl substitution on the transcriptional activation/repression profile of 2,5-dihydro-10-methoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinolines.

Authors:  S W Elmore; M J Coghlan; D D Anderson; J K Pratt; B E Green; A X Wang; M A Stashko; C W Lin; C M Tyree; J N Miner; P B Jacobson; D M Wilcox; B C Lane
Journal:  J Med Chem       Date:  2001-12-06       Impact factor: 7.446

3.  In vitro and in vivo activity of frenolicin B against Plasmodium falciparum and P berghei.

Authors:  Jay T Fitzgerald; Philipp P Henrich; Connor O'Brien; Michael Krause; Eric H Ekland; Corinna Mattheis; Juliana M Sá; David Fidock; Chaitan Khosla
Journal:  J Antibiot (Tokyo)       Date:  2011-10-19       Impact factor: 2.649

4.  Highly efficient cross-dehydrogenative-coupling between ethers and active methylene compounds.

Authors:  Yuhua Zhang; Chao-Jun Li
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-13       Impact factor: 15.336

5.  A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin.

Authors:  Rodney A Fernandes; Vijay P Chavan; Sandip V Mulay; Amarender Manchoju
Journal:  J Org Chem       Date:  2012-10-31       Impact factor: 4.354

6.  Anticoccidial activity of frenolicin B and its derivatives.

Authors:  S Omura; K Tsuzuki; Y Iwai; M Kishi; S Watanabe; H Shimizu
Journal:  J Antibiot (Tokyo)       Date:  1985-10       Impact factor: 2.649

7.  Direct oxa-Pictet-Spengler cyclization to the natural (3a,5)-trans-stereochemistry in the syntheses of (+)-7-deoxyfrenolicin B and (+)-7-deoxykalafungin.

Authors:  Clark N Eid; Jaechul Shim; Jack Bikker; Melissa Lin
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

8.  Carbocyclic frenolicin analogues: novel anticoccidial agents.

Authors:  R E Armer; C J Dutton; B R Fenner; S D Greenwood; K T Hall; A J Rudge
Journal:  Bioorg Med Chem Lett       Date:  1998-01-20       Impact factor: 2.823

9.  Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations.

Authors:  Chao-Jun Li
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

10.  Pyranonaphthoquinone lactones: a new class of AKT selective kinase inhibitors alkylate a regulatory loop cysteine.

Authors:  Edward J Salaski; Girija Krishnamurthy; Wei-Dong Ding; Ker Yu; Shabana S Insaf; Clark Eid; Jaechul Shim; Jeremy I Levin; Keiko Tabei; Lourdes Toral-Barza; Wei-Guo Zhang; Leonard A McDonald; Erick Honores; Cilien Hanna; Ayako Yamashita; Bernard Johnson; Zhong Li; Leif Laakso; Dennis Powell; Tarek S Mansour
Journal:  J Med Chem       Date:  2009-04-23       Impact factor: 7.446
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  6 in total

1.  A divergent enantioselective strategy for the synthesis of griseusins.

Authors:  Yinan Zhang; Qing Ye; Xiachang Wang; Qing-Bai She; Jon S Thorson
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-31       Impact factor: 15.336

2.  Ruthmycin, a new tetracyclic polyketide from Streptomyces sp. RM-4-15.

Authors:  Xiachang Wang; Sherif I Elshahawi; Khaled A Shaaban; Lei Fang; Larissa V Ponomareva; Yinan Zhang; Gregory C Copley; James C Hower; Chang-Guo Zhan; Madan K Kharel; Jon S Thorson
Journal:  Org Lett       Date:  2013-12-16       Impact factor: 6.005

3.  Frenolicin B Targets Peroxiredoxin 1 and Glutaredoxin 3 to Trigger ROS/4E-BP1-Mediated Antitumor Effects.

Authors:  Qing Ye; Yinan Zhang; Yanan Cao; Xiachang Wang; Yubin Guo; Jing Chen; Jamie Horn; Larissa V Ponomareva; Luksana Chaiswing; Khaled A Shaaban; Qiou Wei; Bradley D Anderson; Daret K St Clair; Haining Zhu; Markos Leggas; Jon S Thorson; Qing-Bai She
Journal:  Cell Chem Biol       Date:  2019-01-17       Impact factor: 8.116

Review 4.  Toward ideal carbon dioxide functionalization.

Authors:  Yang Yang; Ji-Woong Lee
Journal:  Chem Sci       Date:  2019-02-20       Impact factor: 9.825

5.  Electroreductive Cobalt-Catalyzed Carboxylation: Cross-Electrophile Electrocoupling with Atmospheric CO2.

Authors:  Nate W J Ang; João C A Oliveira; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-28       Impact factor: 15.336

6.  Total synthesis of griseusins and elucidation of the griseusin mechanism of action.

Authors:  Yinan Zhang; Qing Ye; Larissa V Ponomareva; Yanan Cao; Yang Liu; Zheng Cui; Steven G Van Lanen; S Randal Voss; Qing-Bai She; Jon S Thorson
Journal:  Chem Sci       Date:  2019-06-27       Impact factor: 9.825
  6 in total

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