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Literature DB >> 16928057

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

Abstract

A new protocol for generating aza-ortho-xylylenes via acid-catalyzed or fluoride-promoted ring opening of 2-(2-acylaminophenyl)aziridines is described. This methodology has been exploited in the rapid construction of a hexacyclic substructure of communesin B.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 16928057 PMCID： PMC2547339 DOI： 10.1021/ol061461d

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

14 in total

1. Nomofungin: a new microfilament disrupting agent.

Authors: A S Ratnayake; W Y Yoshida; S L Mooberry; T K Hemscheidt
Journal: J Org Chem Date: 2001-12-28 Impact factor: 4.354

2. New insecticidal compounds, communesins C, D and E, from Penicillium expansum link MK-57.

Authors: Hideo Hayashi; Hirotaka Matsumoto; Kohki Akiyama
Journal: Biosci Biotechnol Biochem Date: 2004-03 Impact factor: 2.043

3. Communesins G and H, new alkaloids from the psychrotolerant fungus Penicillium rivulum.

Authors: Petur W Dalsgaard; John W Blunt; Murray H G Munro; Jens C Frisvad; Carsten Christophersen
Journal: J Nat Prod Date: 2005-02 Impact factor: 4.050

4. Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.

Authors: Brian Chauder; Andrew Larkin; Victor Snieckus
Journal: Org Lett Date: 2002-03-07 Impact factor: 6.005

5. Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy.

Authors: Amos B Smith; Igor G Safonov; R Michael Corbett
Journal: J Am Chem Soc Date: 2002-09-18 Impact factor: 15.419

6. Gold(I)-catalyzed Conia-ene reaction of beta-ketoesters with alkynes.

Authors: Joshua J Kennedy-Smith; Steven T Staben; F Dean Toste
Journal: J Am Chem Soc Date: 2004-04-14 Impact factor: 15.419

7. Brønsted acid-promoted cyclizations of siloxyalkynes with arenes and alkenes.

Authors: Liming Zhang; Sergey A Kozmin
Journal: J Am Chem Soc Date: 2004-08-25 Impact factor: 15.419

8. New communesin derivatives from the fungus Penicillium sp. derived from the Mediterranean sponge Axinella verrucosa.

Authors: Raquel Jadulco; Ru Angelie Edrada; Rainer Ebel; Albrecht Berg; Karsten Schaumann; Victor Wray; Klaus Steube; Peter Proksch
Journal: J Nat Prod Date: 2004-01 Impact factor: 4.050

9. A synthetic approach to nomofungin/communesin B.

Authors: Seth L Crawley; Raymond L Funk
Journal: Org Lett Date: 2003-09-04 Impact factor: 6.005

10. Total synthesis of (+/-)-perophoramidine.

Authors: James R Fuchs; Raymond L Funk
Journal: J Am Chem Soc Date: 2004-04-28 Impact factor: 15.419

10 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. A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors: Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal: Org Lett Date: 2007-10-02 Impact factor: 6.005

Review 3. Chemistry of bridged lactams and related heterocycles.

Authors: Michal Szostak; Jeffrey Aubé
Journal: Chem Rev Date: 2013-06-17 Impact factor: 60.622

4. A highly regio- and stereoselective synthesis of α-fluorinated imides via fluorination of chiral enamides.

Authors: Yan-Shuang Xu; Yu Tang; He-Jing Feng; Ji-Tian Liu; Richard P Hsung
Journal: Org Lett Date: 2015-01-12 Impact factor: 6.005

5. Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters.

Authors: Chung Whan Lee; Seo-Jung Han; Scott C Virgil; Brian M Stoltz
Journal: Tetrahedron Date: 2015-06-03 Impact factor: 2.457