Literature DB >> 15876050

Silicon-directed oxa-Pictet-Spengler cyclization and an unusual dimerization of 2-trimethylsilanyl tryptophols.

Xuqing Zhang1, Xiaojie Li, James C Lanter, Zhihua Sui.   

Abstract

The tetrahydro-pyrano[3,4-b]indoles 6 were synthesized from 2-(2-trimethylsilanyl-1H-indol-3-yl)-ethanols 5 and various ketones or aldehydes through silicon-directed oxa-Pictet-Spengler cyclizations. An unusual reaction led to the dimeric products 7 when some of 5 was treated with acetone using BF(3) as the catalyst.

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Year:  2005        PMID: 15876050     DOI: 10.1021/ol050623n

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


  3 in total

1.  Annulations of enantioenriched allenylsilanes with in situ generated iminium ions: stereoselective synthesis of diverse heterocycles.

Authors:  Ryan A Brawn; James S Panek
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

2.  Biomimetic synthesis of the tetracyclic core of berkelic acid.

Authors:  Jingye Zhou; Barry B Snider
Journal:  Org Lett       Date:  2007-04-28       Impact factor: 6.005

3.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

  3 in total

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