Literature DB >> 19719184

Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations.

M Paola Castaldi1, Dawn M Troast, John A Porco.   

Abstract

The synthesis of spirocyclic oxindole pyran and oxepene frameworks using highly stereoselective Prins cyclizations of homoallylic and bis-homoallylic alcohols and isatin ketals is described.

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Year:  2009        PMID： 19719184      PMCID： PMC2739092          DOI： 10.1021/ol901201k

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


  25 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.  A planning strategy for diversity-oriented synthesis.

Authors:  Martin D Burke; Stuart L Schreiber
Journal:  Angew Chem Int Ed Engl       Date:  2004-01       Impact factor: 15.336

3.  Total synthesis of (+)-dactylolide through an efficient sequential Peterson olefination and Prins cyclization reaction.

Authors:  Danielle L Aubele; Shuangyi Wan; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-30       Impact factor: 15.336

4.  Convergent synthesis of a complex oxime library using chemical domain shuffling.

Authors:  Shun Su; Dayle E Acquilano; Jeevanandam Arumugasamy; Aaron B Beeler; Erin L Eastwood; Joshua R Giguere; Ping Lan; Xiaoguang Lei; Geanna K Min; Adam R Yeager; Ya Zhou; James S Panek; John K Snyder; Scott E Schaus; John A Porco
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

Review 5.  Natural product hybrids as new leads for drug discovery.

Authors:  Lutz F Tietze; Hubertus P Bell; Srivari Chandrasekhar
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-05       Impact factor: 15.336

6.  Novel conversion of 1,2-disubstituted cis-epoxides to one-carbon homologated allylic alcohols using dimethylsulfonium methylide.

Authors:  L Alcaraz; A Cridland; E Kinchin
Journal:  Org Lett       Date:  2001-12-13       Impact factor: 6.005

7.  Aromatic 4-tetrahydropyranyl and 4-quinuclidinyl cations. Linking Prins with Cope and Grob.

Authors:  Roger W Alder; Jeremy N Harvey; Mark T Oakley
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

8.  Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

Authors:  Gary E Keck; Jonathan A Covel; Tobias Schiff; Tao Yu
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

9.  Pteropodine and isopteropodine positively modulate the function of rat muscarinic M(1) and 5-HT(2) receptors expressed in Xenopus oocyte.

Authors:  Tai-Hyun Kang; Kinzo Matsumoto; Michihisa Tohda; Yukihisa Murakami; Hiromitsu Takayama; Mariko Kitajima; Norio Aimi; Hiroshi Watanabe
Journal:  Eur J Pharmacol       Date:  2002-05-24       Impact factor: 4.432

10.  Macrolactonization via Ti(IV)-mediated epoxy-acid coupling: a total synthesis of (-)-dactylolide [and zampanolide].

Authors:  Thomas R Hoye; Min Hu
Journal:  J Am Chem Soc       Date:  2003-08-13       Impact factor: 15.419
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  9 in total

1.  Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.

Authors:  Jacob P MacDonald; Joseph J Badillo; Gary E Arevalo; Abel Silva-García; Annaliese K Franz
Journal:  ACS Comb Sci       Date:  2012-04-02       Impact factor: 3.784

2.  Stereoselective synthesis of tertiary ethers through geometric control of highly substituted oxocarbenium ions.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

3.  Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans.

Authors:  Jingqi Wang; Erika A Crane; Karl A Scheidt
Journal:  Org Lett       Date:  2011-05-18       Impact factor: 6.005

4.  Multicomponent reaction discovery: three-component synthesis of spirooxindoles.

Authors:  Bo Liang; Srinivas Kalidindi; John A Porco; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

5.  Stereocontrolled synthesis of spirooxindoles through Lewis acid-promoted [5 + 2]-annulation of chiral silyl alcohols.

Authors:  Yun Zhang; James S Panek
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

Review 6.  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

7.  Synthesis of a family of spirocyclic scaffolds: building blocks for the exploration of chemical space.

Authors:  Sarvesh Kumar; Paul D Thornton; Thomas O Painter; Prashi Jain; Jared Downard; Justin T Douglas; Conrad Santini
Journal:  J Org Chem       Date:  2013-06-26       Impact factor: 4.354

8.  Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans.

Authors:  Hélio Faustino; Iván Varela; José L Mascareñas; Fernando López
Journal:  Chem Sci       Date:  2015-03-02       Impact factor: 9.825

9.  An oxindole efflux inhibitor potentiates azoles and impairs virulence in the fungal pathogen Candida auris.

Authors:  Kali R Iyer; Kaddy Camara; Martin Daniel-Ivad; Richard Trilles; Sheila M Pimentel-Elardo; Jen L Fossen; Karen Marchillo; Zhongle Liu; Shakti Singh; José F Muñoz; Sang Hu Kim; John A Porco; Christina A Cuomo; Noelle S Williams; Ashraf S Ibrahim; John E Edwards; David R Andes; Justin R Nodwell; Lauren E Brown; Luke Whitesell; Nicole Robbins; Leah E Cowen
Journal:  Nat Commun       Date:  2020-12-22       Impact factor: 14.919
  9 in total

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