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Synthesis 1989; 1989(2): 89-92
DOI: 10.1055/s-1989-27160
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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
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Publication Date:
17 September 2002 (online)

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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.

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