Literature DB >> 20161277

Metathesis Cascade Strategies (ROM-RCM-CM): A DOS approach to Skeletally Diverse Sultams.

Kyu Ok Jeon1, Dinesh Rayabarapu, Alan Rolfe, Kelly Volp, Iman Omar, Paul R Hanson.   

Abstract

The development of a ring-opening metathesis/ring-closing metathesis/cross metathesis (ROM-RCM-CM) cascade strategy to the synthesis of a diverse collection of bi- and tricyclic sultams is reported. In this study, functionalized sultam scaffolds derived from intramolecular Diels-Alder (IMDA) reactions undergo metathesis cascades to yield a collection tricyclic sultams. Additional appendage based diversity was achieved by utilizing a variety of CM partners.

Entities:  

Year:  2009        PMID： 20161277      PMCID： PMC2702866          DOI： 10.1016/j.tet.2009.03.080

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  31 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.  Pairwise use of complexity-generating reactions in diversity-oriented organic synthesis.

Authors:  D Lee; J K Sello; S L Schreiber
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

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

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

4.  Skeletal diversity construction via a branching synthetic strategy.

Authors:  Emma E Wyatt; Suzanne Fergus; Warren R J D Galloway; Andreas Bender; David J Fox; Alleyn T Plowright; Alan S Jessiman; Martin Welch; David R Spring
Journal:  Chem Commun (Camb)       Date:  2006-07-10       Impact factor: 6.222

5.  Concise and diversity-oriented synthesis of novel scaffolds embedded with privileged benzopyran motif.

Authors:  Sung Kon Ko; Hwan Jong Jang; Eunha Kim; Seung Bum Park
Journal:  Chem Commun (Camb)       Date:  2006-06-13       Impact factor: 6.222

Review 6.  The remarkable metal-catalysed olefin metathesis reaction.

Authors:  Amir H Hoveyda; Adil R Zhugralin
Journal:  Nature       Date:  2007-11-08       Impact factor: 49.962

7.  Efficient enantioselective synthesis of piperidines through catalytic asymmetric ring-opening/cross-metathesis reactions.

Authors:  G Alex Cortez; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 8.  Diversity-oriented synthesis; a spectrum of approaches and results.

Authors:  Richard J Spandl; Andreas Bender; David R Spring
Journal:  Org Biomol Chem       Date:  2008-02-19       Impact factor: 3.876

9.  Selective ring opening cross metathesis of cyclooctadiene and trisubstituted cycloolefins.

Authors:  John P Morgan; Christie Morrill; Robert H Grubbs
Journal:  Org Lett       Date:  2002-01-10       Impact factor: 6.005

10.  Design and synthesis of 8-hydroxy-[1,6]naphthyridines as novel inhibitors of HIV-1 integrase in vitro and in infected cells.

Authors:  Linghang Zhuang; John S Wai; Mark W Embrey; Thorsten E Fisher; Melissa S Egbertson; Linda S Payne; James P Guare; Joseph P Vacca; Daria J Hazuda; Peter J Felock; Abigail L Wolfe; Kara A Stillmock; Marc V Witmer; Gregory Moyer; William A Schleif; Lori J Gabryelski; Yvonne M Leonard; Joseph J Lynch; Stuart R Michelson; Steven D Young
Journal:  J Med Chem       Date:  2003-02-13       Impact factor: 7.446
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  12 in total

1.  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

2.  Synthesis of epoxybenzo[d]isothiazole 1,1-dioxides via a reductive-Heck, metathesis-sequestration protocol.

Authors:  Naeem Asad; Paul R Hanson; Toby R Long; Dinesh K Rayabarapu; Alan Rolfe
Journal:  Chem Commun (Camb)       Date:  2011-07-05       Impact factor: 6.222

3.  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

4.  Synthesis of amino-benzothiaoxazepine-1,1-dioxides utilizing a microwave-assisted, S(N)Ar protocol.

Authors:  Alan Rolfe; Farman Ullah; Thiwanka B Samarakoon; Ryan D Kurtz; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Conrad Santini; Michael G Organ; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2011-09-08       Impact factor: 3.784

5.  Reagent based DOS: a "Click, Click, Cyclize" strategy to probe chemical space.

Authors:  Alan Rolfe; Gerald H Lushington; Paul R Hanson
Journal:  Org Biomol Chem       Date:  2010-03-16       Impact factor: 3.876

6.  Automated synthesis of a 184-member library of thiadiazepan-1,1-dioxide-4-ones.

Authors:  Erik Fenster; Toby R Long; Qin Zang; David Hill; Benjamin Neuenswander; Gerald H Lushington; Aihua Zhou; Conrad Santini; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2011-02-10       Impact factor: 3.784

7.  Scaling out by microwave-assisted, continuous flow organic synthesis (MACOS): multi-gram synthesis of bromo- and fluoro-benzofused sultams benzthiaoxazepine-1,1-dioxides.

Authors:  Farman Ullah; Thiwanka Samarakoon; Alan Rolfe; Ryan D Kurtz; Paul R Hanson; Michael G Organ
Journal:  Chemistry       Date:  2010-09-24       Impact factor: 5.236

8.  A modular reaction pairing approach to the diversity-oriented synthesis of fused- and bridged-polycyclic sultams.

Authors:  Thiwanka B Samarakoon; Joanna K Loh; Alan Rolfe; Lisa S Le; Sun Young Yoon; Gerald H Lushington; Paul R Hanson
Journal:  Org Lett       Date:  2011-09-07       Impact factor: 6.005

9.  Synthesis of a stereochemically diverse library of medium-sized lactams and sultams via S(N)Ar cycloetherification.

Authors:  Baudouin Gerard; Jeremy R Duvall; Jason T Lowe; Tiffanie Murillo; Jingqiang Wei; Lakshmi B Akella; Lisa A Marcaurelle
Journal:  ACS Comb Sci       Date:  2011-04-28       Impact factor: 3.784

10.  One-pot, three-component, domino Heck-aza-Michael approach to libraries of functionalized 1,1-dioxido-1,2-benzisothiazoline-3-acetic acids.

Authors:  Alan Rolfe; Kyle Young; Kelly Volp; Frank Schoenen; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson
Journal:  J Comb Chem       Date:  2009 Jul-Aug
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