Literature DB >> 19115841

"Click, click, cyclize": a DOS approach to sultams utilizing vinyl sulfonamide linchpins.

Aihua Zhou1, Dinesh Rayabarapu, Paul R Hanson.   

Abstract

A diversity-oriented synthesis (DOS) strategy termed "Click, Click, Cyclize" is reported. This approach relies on functional group (FG) pairing between a vinyl sulfonamide and an array of functional groups to synthesize skeletally diverse sultams. Several FG pairing pathways on central tertiary vinyl sulfonamide linchpins have been developed including intramolecular Heck, aza-Michael, ring-closing enyne metathesis, Pauson-Khand, and chemoselective oxidation/Baylis-Hillman reactions.

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Year:  2009        PMID： 19115841      PMCID： PMC2742886          DOI： 10.1021/ol802467f

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


  27 in total

Review 1.  Target-oriented and diversity-oriented organic synthesis in drug discovery.

Authors:  S L Schreiber
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

2.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors:  Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

3.  Use of biomimetic diversity-oriented synthesis to discover galanthamine-like molecules with biological properties beyond those of the natural product.

Authors:  H E Pelish; N J Westwood; Y Feng; T Kirchhausen; M D Shair
Journal:  J Am Chem Soc       Date:  2001-07-11       Impact factor: 15.419

4.  Diversity-oriented synthesis; a challenge for synthetic chemists.

Authors:  David R Spring
Journal:  Org Biomol Chem       Date:  2003-11-21       Impact factor: 3.876

Review 5.  Exploring new chemical space by stereocontrolled diversity-oriented synthesis.

Authors:  Prabhat Arya; Reni Joseph; Zhonghong Gan; Bojana Rakic
Journal:  Chem Biol       Date:  2005-02

6.  Small-molecule inhibitors of protein geranylgeranyltransferase type I.

Authors:  Sabrina Castellano; Hannah D G Fiji; Sape S Kinderman; Masaru Watanabe; Pablo de Leon; Fuyuhiko Tamanoi; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2007-04-17       Impact factor: 15.419

7.  An approach to skeletal diversity using functional group pairing of multifunctional scaffolds.

Authors:  Eamon Comer; Erin Rohan; Li Deng; John A Porco
Journal:  Org Lett       Date:  2007-05-02       Impact factor: 6.005

8.  Synthesis of cyclic sulfonamides through intramolecular Diels-Alder reactions.

Authors:  I R Greig; M J Tozer; P T Wright
Journal:  Org Lett       Date:  2001-02-08       Impact factor: 6.005

9.  Dipeptide vinyl sultams: synthesis via the Wittig-Horner reaction and activity against papain, falcipain-2 and Plasmodium falciparum.

Authors:  Cláudia Valente; Rita C Guedes; Rui Moreira; Jim Iley; Jiri Gut; Philip J Rosenthal
Journal:  Bioorg Med Chem Lett       Date:  2006-05-12       Impact factor: 2.823

10.  Diversity-oriented synthesis of azaspirocycles.

Authors:  Peter Wipf; Corey R J Stephenson; Maciej A A Walczak
Journal:  Org Lett       Date:  2004-08-19       Impact factor: 6.005
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  29 in total

1.  Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules.

Authors:  Warren R J D Galloway; Albert Isidro-Llobet; David R Spring
Journal:  Nat Commun       Date:  2010-09-21       Impact factor: 14.919

2.  A summary of seven- and eight-membered ring sultam syntheses via three Michael addition reactions.

Authors:  Ben Niu; Ping Xie; Min Wang; Yanjie Wang; Wannian Zhao; Charles U Pittman; Aihua Zhou
Journal:  Mol Divers       Date:  2015-04-03       Impact factor: 2.943

3.  Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.

Authors:  Alan Rolfe; Thiwanka B Samarakoon; Paul R Hanson
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

4.  Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.

Authors:  Qin Zang; Salim Javed; Patrick Porubsky; Farman Ullah; Benjamin Neuenswander; Gerald H Lushington; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2012-02-06       Impact factor: 3.784

5.  Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 2: Routes to Bicyclic Sultams.

Authors:  Qin Zang; Salim Javed; Aihua Zhou; Chris A Knudtson; Danse Bi; Fatima Z Basha; Paul R Hanson
Journal:  Heterocycles       Date:  2012-12-31       Impact factor: 0.831

6.  Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol.

Authors:  Qin Zang; Aihua Zhou; Salim Javed; Pradip K Maity; Chris A Knudtson; Danse Bi; Jared J Hastings; Fatima Z Basha; Paul R Hanson
Journal:  Heterocycles       Date:  2012-12-31       Impact factor: 0.831

Review 7.  Chemistry of bridged lactams and related heterocycles.

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

8.  Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy.

Authors:  Alan Rolfe; Paul R Hanson
Journal:  Tetrahedron Lett       Date:  2009-12-16       Impact factor: 2.415

9.  Triazole-containing isothiazolidine 1,1-dioxide library synthesis: one-pot, multi-component protocols for small molecular probe discovery.

Authors:  Alan Rolfe; Thomas O Painter; Naeem Asad; Moon Young Hur; Kyu Ok Jeon; Marek Brzozowski; Sarra V Klimberg; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2011-08-25       Impact factor: 3.784

10.  Stereochemical and skeletal diversity arising from amino propargylic alcohols.

Authors:  Daniela Pizzirani; Taner Kaya; Paul A Clemons; Stuart L Schreiber
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005
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