Literature DB >> 11784175

A new route to spiropyrrolidinyl-oxindole alkaloids via iodide ion induced rearrangement of [(N-aziridinomethylthio)methylene]-2-oxindoles.

U K Syam Kumar1, H Ila, H Junjappa.   

Abstract

A new approach for the synthesis of spiropyrrolidinyloxindole alkaloids, i.e. coerulescine (4) and horsfiline (5) has been developed via iodide ion induced rearrangement of [(N-aziridinomethylthio)methylene]oxindoles 2 to the respective spiropyrroline-2-oxindole derivatives 3 and their subsequent one-pot reductive dethiomethylation-N-methylation. [reaction: see text]

Entities:  

Year:  2001        PMID： 11784175     DOI： 10.1021/ol016824i

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


  4 in total

1.  Rh(II)2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides.

Authors:  Ashley L Pumphrey; Huijun Dong; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline.

Authors:  Barry M Trost; Megan K Brennan
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

3.  Total synthesis of (±)-coerulescine and (±)-horsfiline.

Authors:  Mukund G Kulkarni; Attrimuni P Dhondge; Sanjay W Chavhan; Ajit S Borhade; Yunnus B Shaikh; Deekshaputra R Birhade; Mayur P Desai; Nagorao R Dhatrak
Journal:  Beilstein J Org Chem       Date:  2010-09-27       Impact factor: 2.883

4.  Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters.

Authors:  Satish S More; T Krishna Mohan; Y Sateesh Kumar; U K Syam Kumar; Navin B Patel
Journal:  Beilstein J Org Chem       Date:  2011-06-20       Impact factor: 2.883
  4 in total

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