Download PDF
Synthesis 1995; 1995(6): 607-626
DOI: 10.1055/s-1995-3983
review
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Furan-, Pyrrole-, and Thiophene-Based Siloxydienes for Syntheses of Densely Functionalized Homochiral Compounds

Giovanni Casiraghi* , Gloria Rassu
  • *Dipartimento Farmaceutico, Università di Parma, I-43100 Parma, Italy, Fax +39(521)905006; E-mail: casirag@ipruniv.cce.unipr.it
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

This review describes the methods of preparation and use of 2-(trimethylsiloxy)furan, N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole, and certain substituted analogues and congeners, including novel 2-(tert-butyldimethylsiloxy)thiophene, to synthesize complex carbohydrates, azasugars, polyhydroxylated alkaloids, C-glycosylated α-amino acids, amino acids bearing quaternary chiral carbon atoms, and thiosugars. Especially emphasized is the preparation of enantiomerically pure compounds of biological interest. Some mechanistic insights are presented.

The aldol-type condensations of the title siloxydienes with chiral electrophilic reagents produce versatile templates to be exploited to synthesize a myriad of multifunctional compounds