Literature DB >> 22920858

Total synthesis of (±)-hirsutine: application of phosphine-catalyzed imine-allene [4 + 2] annulation.

Reymundo A Villa1, Qihai Xu, Ohyun Kwon.   

Abstract

The total synthesis of the indole alkaloid hirsutine has been achieved, with a key step being the application of our phosphine-catalyzed [4 + 2] annulation of an imine with ethyl α-methylallenoate. From commercially available indole-2-carboxaldehyde, the target was synthesized in 14 steps and 6.7% overall yield.

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Year:  2012        PMID： 22920858      PMCID： PMC3439149          DOI： 10.1021/ol302077n

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


  17 in total

1.  Effects of hirsutine and dihydrocorynantheine on the action potentials of sino-atrial node, atrium and ventricle.

Authors:  H Masumiya; T Saitoh; Y Tanaka; S Horie; N Aimi; H Takayama; H Tanaka; K Shigenobu
Journal:  Life Sci       Date:  1999       Impact factor: 5.037

2.  Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death.

Authors:  Y Shimada; H Goto; T Kogure; N Shibahara; I Sakakibara; H Sasaki; K Terasawa
Journal:  Am J Chin Med       Date:  2001       Impact factor: 4.667

3.  Evaluation of the protective effects of alkaloids isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death in cultured cerebellar granule cells from rats.

Authors:  Y Shimada; H Goto; T Itoh; I Sakakibara; M Kubo; H Sasaki; K Terasawa
Journal:  J Pharm Pharmacol       Date:  1999-06       Impact factor: 3.765

4.  General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids.

Authors:  Alexander Deiters; Martin Pettersson; Stephen F Martin
Journal:  J Org Chem       Date:  2006-08-18       Impact factor: 4.354

5.  Anticonvulsant effect of Uncaria rhynchophylla (Miq) Jack. in rats with kainic acid-induced epileptic seizure.

Authors:  C L Hsieh; M F Chen; T C Li; S C Li; N Y Tang; C T Hsieh; C Z Pon; J G Lin
Journal:  Am J Chin Med       Date:  1999       Impact factor: 4.667

6.  PHOSPHINE-CATALYZED [4+2] ANNULATION: SYNTHESIS OF ETHYL 6-PHENYL-1-TOSYL-1,2,5,6-TETRAHYDROPYRIDINE-3-CARBOXYLATE.

Authors:  Kui Lu; Ohyun Kwon; Kay M Brummond; Matthew M Davis
Journal:  Organic Synth       Date:  2009-03-01

7.  An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines.

Authors:  Xue-Feng Zhu; Jie Lan; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2003-04-23       Impact factor: 15.419

8.  Total synthesis of (+/-)-perophoramidine.

Authors:  James R Fuchs; Raymond L Funk
Journal:  J Am Chem Soc       Date:  2004-04-28       Impact factor: 15.419

9.  [Vasodilative effects of indole alkaloids obtained from domestic plants, Uncaria rhynchophylla Miq. and Amsonia elliptica Roem. et Schult].

Authors:  Y Ozaki
Journal:  Nihon Yakurigaku Zasshi       Date:  1990-02

10.  Rhodium-catalyzed methylenation of aldehydes.

Authors:  Hélène Lebel; Valérie Paquet
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419
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  10 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.

Authors:  Yumei Xiao; Hongchao Guo; Ohyun Kwon
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

3.  Discussion Addendum for: Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Ethyl 6-Phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate.

Authors:  Aslam C Shaikh; Ohyun Kwon
Journal:  Organic Synth       Date:  2019-04-22

4.  A torquoselective 6π electrocyclization approach to reserpine alkaloids.

Authors:  Gregg A Barcan; Ashay Patel; K N Houk; Ohyun Kwon
Journal:  Org Lett       Date:  2012-10-05       Impact factor: 6.005

5.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2013-12-25       Impact factor: 6.222

Review 6.  Phosphine catalysis of allenes with electrophiles.

Authors:  Zhiming Wang; Xingzhu Xu; Ohyun Kwon
Journal:  Chem Soc Rev       Date:  2014-03-24       Impact factor: 54.564

7.  Iron-catalyzed Cross-Coupling of Propargyl Carboxylates and Grignard Reagents: Synthesis of Substituted Allenes.

Authors:  Simon N Kessler; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-17       Impact factor: 15.336

8.  Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines: a facile synthesis of tetrahydropyridines.

Authors:  Leijie Zhou; Chunhao Yuan; Yuan Zeng; Honglei Liu; Chang Wang; Xing Gao; Qijun Wang; Cheng Zhang; Hongchao Guo
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

Review 9.  Organophosphine-Catalyzed [4C+X] Annulations.

Authors:  Yangyan Li; Xiang Chen; Xiaoming Chen; Xiao Shen
Journal:  Molecules       Date:  2018-11-19       Impact factor: 4.411

10.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036
  10 in total

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