Literature DB >> 19053717

Formal synthesis of (+/-)-roseophilin.

Abdallah Y Bitar1, Alison J Frontier.   

Abstract

A formal synthesis of (+/-)-roseophilin is described. Scandium(III)-catalyzed Nazarov cyclization of 2,5-disubstituted N-tosylpyrrole 19 gives a 5,5'-fused ketopyrrole, and ansa-bridge formation via pi-allyl palladium macrocyclization gives 21.

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Year:  2009        PMID： 19053717      PMCID： PMC2646896          DOI： 10.1021/ol802329y

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


  17 in total

1.  Studies on DNA cleavage by cytotoxic pyrrole alkaloids reveal the distinctly different behavior of roseophilin and prodigiosin derivatives.

Authors:  A Fürstner; E J Grabowski
Journal:  Chembiochem       Date:  2001-09-03       Impact factor: 3.164

Review 2.  Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years.

Authors:  Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2003-08-11       Impact factor: 15.336

3.  A formal total synthesis of roseophilin: cyclopentannelation approach to the macrocyclic core.

Authors:  P E Harrington; M A Tius
Journal:  Org Lett       Date:  1999-08-26       Impact factor: 6.005

4.  A ring-expansion approach to roseophilin.

Authors:  Samuel G Salamone; Gregory B Dudley
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

5.  Remote stereocontrol in the Nazarov reaction: a new approach to the core of roseophilin.

Authors:  Ernesto G Occhiato; Cristina Prandi; Alessandro Ferrali; Antonio Guarna
Journal:  J Org Chem       Date:  2005-05-27       Impact factor: 4.354

6.  Asymmetric total synthesis of ent-(-)-roseophilin: assignment of absolute configuration.

Authors:  D L Boger; J Hong
Journal:  J Am Chem Soc       Date:  2001-09-05       Impact factor: 15.419

7.  The first examples of Nazarov cyclizations leading to annulated pyrroles.

Authors:  Chuanjun Song; David W Knight; Maria A Whatton
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

8.  Polarizing the Nazarov cyclization: the impact of dienone substitution pattern on reactivity and selectivity.

Authors:  Wei He; Ildiko R Herrick; Tulay A Atesin; Patrick A Caruana; Colleen A Kellenberger; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

9.  Ligand binding in a docking site of cytochrome C oxidase: a time-resolved step-scan Fourier transform infrared study.

Authors:  Constantinos Koutsoupakis; Tewfik Soulimane; Constantinos Varotsis
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419

10.  A Torquoselective Extrusion of Isoxazoline N-Oxides. Application to the Synthesis of Aryl Vinyl and Divinyl Ketones for Nazarov Cyclization.

Authors:  Daniel P Canterbury; Ildiko R Herrick; Joann Um; K N Houk; Alison J Frontier
Journal:  Tetrahedron       Date:  2009-04-18       Impact factor: 2.457
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  12 in total

1.  Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

Authors:  David Lebœuf; Jie Huang; Vincent Gandon; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-26       Impact factor: 15.336

2.  An organocatalytic asymmetric Nazarov cyclization.

Authors:  Ashok K Basak; Naoyuki Shimada; William F Bow; David A Vicic; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

3.  Neutral Nazarov-type cyclization catalyzed by palladium(0).

Authors:  Naoyuki Shimada; Craig Stewart; William F Bow; Anais Jolit; Kahoano Wong; Zhe Zhou; Marcus A Tius
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

4.  Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

5.  A highly reactive dicationic iridium(III) catalyst for the polarized Nazarov cyclization reaction.

Authors:  Tulaza Vaidya; Abdurrahman C Atesin; Ildiko R Herrick; Alison J Frontier; Richard Eisenberg
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-26       Impact factor: 15.336

6.  Experimental and theoretical studies on the Nazarov cyclization/Wagner-Meerwein rearrangement sequence.

Authors:  David Lebœuf; Vincent Gandon; Jennifer Ciesielski; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2012-04-03       Impact factor: 15.419

7.  Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

Authors:  Jie Huang; David Lebœuf; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2011-04-05       Impact factor: 15.419

8.  Modular access to complex prodiginines: total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer.

Authors:  James H Frederich; Patrick G Harran
Journal:  J Am Chem Soc       Date:  2013-03-01       Impact factor: 15.419

9.  α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

Authors:  Zhi-Xiong Ma; Shuzhong He; Wangze Song; Richard P Hsung
Journal:  Org Lett       Date:  2012-11-02       Impact factor: 6.005

Review 10.  Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products.

Authors:  Dennis X Hu; David M Withall; Gregory L Challis; Regan J Thomson
Journal:  Chem Rev       Date:  2016-06-17       Impact factor: 60.622
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