Literature DB >> 20356070

The tert-butylsulfinamide lynchpin in transition-metal-mediated multiscaffold library synthesis.

Renato A Bauer1, Christine M DiBlasi, Derek S Tan.   

Abstract

A unified synthetic approach to diverse polycyclic scaffolds has been developed using transition-metal-mediated cycloaddition and cyclization reactions of enynes and diynes. The tert-butylsulfinamide group has been identified as a particularly versatile lynchpin in these reactions, with a reactivity profile uniquely suited for efficient, stereoselective substrate synthesis and downstream transformations. This approach provides 10 distinct, functionalized scaffold classes related to common core structures in alkaloid and terpenoid natural products.

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Year:  2010        PMID： 20356070      PMCID： PMC2869296          DOI： 10.1021/ol100574y

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


  34 in total

1.  Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives.

Authors:  S Saito; Y Yamamoto
Journal:  Chem Rev       Date:  2000-08-09       Impact factor: 60.622

2.  Synthetic strategy toward skeletal diversity via solid-supported, otherwise unstable reactive intermediates.

Authors:  Steven J Taylor; Alexander M Taylor; Stuart L Schreiber
Journal:  Angew Chem Int Ed Engl       Date:  2004-03-19       Impact factor: 15.336

3.  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

4.  Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters.

Authors:  Melissa A Beenen; Daniel J Weix; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

5.  Hydrogen-mediated reductive coupling of conjugated alkynes with ethyl (N-Sulfinyl)iminoacetates: synthesis of unnatural alpha-amino acids via rhodium-catalyzed C-C bond forming hydrogenation.

Authors:  Jong-Rock Kong; Chang-Woo Cho; Michael J Krische
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

6.  Novel sulfinyl imine ligands for asymmetric catalysis.

Authors:  Laurie B Schenkel; Jonathan A Ellman
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

7.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Application of P,N-sulfinyl imine ligands to iridium-catalyzed asymmetric hydrogenation of olefins.

Authors:  Laurie B Schenkel; Jonathan A Ellman
Journal:  J Org Chem       Date:  2004-03-19       Impact factor: 4.354

9.  tert-Butanesulfinimines: structure, synthesis and synthetic applications.

Authors:  Franck Ferreira; Candice Botuha; Fabrice Chemla; Alejandro Pérez-Luna
Journal:  Chem Soc Rev       Date:  2009-01-26       Impact factor: 54.564

Review 10.  Towards the optimal screening collection: a synthesis strategy.

Authors:  Thomas E Nielsen; Stuart L Schreiber
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
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  12 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.  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

3.  Diversity-oriented synthesis of macrocyclic peptidomimetics.

Authors:  Albert Isidro-Llobet; Tiffanie Murillo; Paula Bello; Agostino Cilibrizzi; James T Hodgkinson; Warren R J D Galloway; Andreas Bender; Martin Welch; David R Spring
Journal:  Proc Natl Acad Sci U S A       Date:  2011-03-07       Impact factor: 11.205

4.  Solid-phase synthesis and chemical space analysis of a 190-membered alkaloid/terpenoid-like library.

Authors:  Gustavo Moura-Letts; Christine M Diblasi; Renato A Bauer; Derek S Tan
Journal:  Proc Natl Acad Sci U S A       Date:  2011-03-30       Impact factor: 11.205

5.  Cheminformatic comparison of approved drugs from natural product versus synthetic origins.

Authors:  Christopher F Stratton; David J Newman; Derek S Tan
Journal:  Bioorg Med Chem Lett       Date:  2015-07-14       Impact factor: 2.823

6.  Synthesis and profiling of a diverse collection of azetidine-based scaffolds for the development of CNS-focused lead-like libraries.

Authors:  Jason T Lowe; Maurice D Lee; Lakshmi B Akella; Emeline Davoine; Etienne J Donckele; Landon Durak; Jeremy R Duvall; Baudouin Gerard; Edward B Holson; Adrien Joliton; Sarathy Kesavan; Berenice C Lemercier; Haibo Liu; Jean-Charles Marié; Carol A Mulrooney; Giovanni Muncipinto; Morgan Welzel-O'Shea; Laura M Panko; Ann Rowley; Byung-Chul Suh; Meryl Thomas; Florence F Wagner; Jingqiang Wei; Michael A Foley; Lisa A Marcaurelle
Journal:  J Org Chem       Date:  2012-08-10       Impact factor: 4.354

Review 7.  Recent advances in the development of polycyclic skeletons via Ugi reaction cascades.

Authors:  Jie Lei; Jiang-Ping Meng; Dian-Yong Tang; Brendan Frett; Zhong-Zhu Chen; Zhi-Gang Xu
Journal:  Mol Divers       Date:  2018-01-16       Impact factor: 2.943

Review 8.  Cheminformatic analysis of natural product-based drugs and chemical probes.

Authors:  Samantha Stone; David J Newman; Steven L Colletti; Derek S Tan
Journal:  Nat Prod Rep       Date:  2022-01-26       Impact factor: 13.423

9.  Parallel and four-step synthesis of natural-product-inspired scaffolds through modular assembly and divergent cyclization.

Authors:  Hiroki Oguri; Haruki Mizoguchi; Hideaki Oikawa; Aki Ishiyama; Masato Iwatsuki; Kazuhiko Otoguro; Satoshi Omura
Journal:  Beilstein J Org Chem       Date:  2012-06-22       Impact factor: 2.883

10.  A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes.

Authors:  Chuan-Jin Hou; Alexander W Schuppe; James Levi Knippel; Anton Z Ni; Stephen L Buchwald
Journal:  Org Lett       Date:  2021-11-02       Impact factor: 6.072
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