Download PDF
Synthesis 1989; 1989(2): 89-92
DOI: 10.1055/s-1989-27160
paper
© 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.

Total Synthesis of Protected D-altro- and D-galacto-3,6-Dideoxy-3-C-methylhexoses; Key Intermediates of a Rifamycin S Synthesis

Gerhard Tarara* , Dieter Hoppe
  • *Institut für Organische Chemie der Universität Kiel, Olshausenstr, 40 -60, D-2300 Kiel 1, Federal Republic of Germany
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Two particular derivatives of the title compound, used in the Kinoshita synthesis of the Rifamycin S ansa chain, were prepared by total synthesis from isobutyl (R)-lactate. The best conditions were worked out for the inversion of the 2-hydroxy group in the appropriate α-D-allo- and β-D-talofuranosides, readily available with few steps from (R)-2-benzyloxypropanal by the homoaldol reaction, with an α-metalated (E)-2-butenyl carbamate.