Literature DB >> 21591768

Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans.

Jingqi Wang1, Erika A Crane, Karl A Scheidt.   

Abstract

A Brønsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a β-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.
© 2011 American Chemical Society

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Year:  2011        PMID： 21591768      PMCID： PMC3115630          DOI： 10.1021/ol200987c

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


  32 in total

1.  Novel, one-pot, three-component route to indol-3-yl substituted spirooxindole derivatives.

Authors:  Tao Chen; Xiao-Ping Xu; Shun-Jun Ji
Journal:  J Comb Chem       Date:  2010-09-13

2.  TiCl4 catalyzed tandem construction of C-C and C-O bonds: a simple and one-pot atom-economical stereoselective synthesis of spiro-oxindoles.

Authors:  Deevi Basavaiah; Jamjanam Srivardhana Rao; Raju Jannapu Reddy; Anumolu Jaganmohan Rao
Journal:  Chem Commun (Camb)       Date:  2005-04-06       Impact factor: 6.222

3.  Total synthesis and structure-activity investigation of the marine natural product neopeltolide.

Authors:  Daniel W Custar; Thomas P Zabawa; John Hines; Craig M Crews; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

4.  Concise syntheses of the abyssinones and discovery of new inhibitors of prostate cancer and MMP-2 expression.

Authors:  Rebecca L Farmer; Margaret M Biddle; Antoinette E Nibbs; Xiaoke Huang; Raymond C Bergan; Karl A Scheidt
Journal:  ACS Med Chem Lett       Date:  2010-11-11       Impact factor: 4.345

5.  Stereoselectivity and regioselectivity in the segment-coupling Prins cyclization.

Authors:  J J Jaber; K Mitsui; S D Rychnovsky
Journal:  J Org Chem       Date:  2001-06-29       Impact factor: 4.354

6.  Off-center oxygen-arene interactions in solution: a quantitative study.

Authors:  Benjamin W Gung; Xiaowen Xue; Hans J Reich
Journal:  J Org Chem       Date:  2005-09-02       Impact factor: 4.354

7.  Total synthesis and structural revision of the marine macrolide neopeltolide.

Authors:  Daniel W Custar; Thomas P Zabawa; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

8.  Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins.

Authors:  Ryo Shintani; Shin-ya Hayashi; Masataka Murakami; Momotaro Takeda; Tamio Hayashi
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

Review 9.  Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

Authors:  Chris V Galliford; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences.

Authors:  Benito Alcaide; Pedro Almendros; Raquel Rodríguez-Acebes
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354
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  9 in total

1.  Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones.

Authors:  Joseph J Badillo; Abel Silva-García; Benjamin H Shupe; James C Fettinger; Annaliese K Franz
Journal:  Tetrahedron Lett       Date:  2011-10-26       Impact factor: 2.415

2.  Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.

Authors:  R Frederick Lambert; Robert J Hinkle; Stephen E Ammann; Yajing Lian; Jia Liu; Shane E Lewis; Robert D Pike
Journal:  J Org Chem       Date:  2011-10-25       Impact factor: 4.354

3.  Catalytic enantioselective synthesis of 2-aryl-chromenes.

Authors:  Bi-Shun Zeng; Xinyi Yu; Paul W Siu; Karl A Scheidt
Journal:  Chem Sci       Date:  2014-06       Impact factor: 9.825

4.  An N-heterocyclic carbene/Lewis acid strategy for the stereoselective synthesis of spirooxindole lactones.

Authors:  Julien Dugal-Tessier; Elizabeth A O'Bryan; Thomas B H Schroeder; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

Review 5.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

6.  A Biocatalytic Route to Highly Enantioenriched β-Hydroxydioxinones.

Authors:  Rick C Betori; Eric R Miller; Karl A Scheidt
Journal:  Adv Synth Catal       Date:  2017-03-02       Impact factor: 5.837

7.  Asymmetric Aldol Reaction of 3-Acetyl-2H-chromen-2-ones and Isatins Catalyzed by a Bifunctional Quinidine Urea Catalyst.

Authors:  Santhi Abbaraju; John Cong-Gui Zhao
Journal:  Adv Synth Catal       Date:  2014-01-13       Impact factor: 5.837

8.  An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans.

Authors:  Ansoo Lee; Rick C Betori; Erika A Crane; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2018-05-10       Impact factor: 15.419

9.  Highly Efficient and Stereoselective Construction of Bispirooxindole Derivatives via a Three-Component 1,3-Dipolar Cycloaddition Reaction.

Authors:  Qin Xu; De Wang; Yin Wei; Min Shi
Journal:  ChemistryOpen       Date:  2014-06-18       Impact factor: 2.911
  9 in total

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