Literature DB >> 12943379

A synthetic approach to nomofungin/communesin B.

Seth L Crawley1, Raymond L Funk.   

Abstract

[reaction: see text] A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an ortho-quinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.

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Year:  2003        PMID： 12943379     DOI： 10.1021/ol034407v

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


  17 in total

Review 1.  Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

Authors:  Barry M Trost; Maksim Osipov
Journal:  Chemistry       Date:  2015-09-10       Impact factor: 5.236

2.  Total synthesis of the polycyclic fungal metabolite (+/-)-communesin F.

Authors:  Peng Liu; Jae Hong Seo; Steven M Weinreb
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-08       Impact factor: 15.336

3.  Evolution of a strategy for total synthesis of the marine fungal alkaloid (+/-)-communesin F.

Authors:  Jae Hong Seo; Peng Liu; Steven M Weinreb
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

Review 4.  Oxidative Cyclization in Natural Product Biosynthesis.

Authors:  Man-Cheng Tang; Yi Zou; Kenji Watanabe; Christopher T Walsh; Yi Tang
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

5.  P450-Mediated Coupling of Indole Fragments To Forge Communesin and Unnatural Isomers.

Authors:  Hsiao-Ching Lin; Travis C McMahon; Ashay Patel; Michael Corsello; Adam Simon; Wei Xu; Muxun Zhao; K N Houk; Neil K Garg; Yi Tang
Journal:  J Am Chem Soc       Date:  2016-03-18       Impact factor: 15.419

6.  Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines: application in the construction of the communesin ring system.

Authors:  Seth L Crawley; Raymond L Funk
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

Review 7.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

8.  Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.

Authors:  Kuan-Lin Chen; Chen-Yu Lai; Mai-Truc Pham; Rong-Jie Chein; Yi Tang; Hsiao-Ching Lin
Journal:  Org Lett       Date:  2020-04-03       Impact factor: 6.005

9.  Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.

Authors:  Alex W Schammel; Grace Chiou; Neil K Garg
Journal:  Org Lett       Date:  2012-08-20       Impact factor: 6.005

10.  Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine.

Authors:  Nicholas R Perl; Nathan D Ide; Sudeep Prajapati; Hahdi H Perfect; Sergio G Durón; David Y Gin
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419
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