Infoscience

Journal article

Total asymmetric synthesis of seco-acids of 9,12-anhydroerythronolide aglycons

The Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'S)-camphanate was converted into (2R,3R,4S,5S,6R,7R)-3,6-epoxy-4,5-isopropylidenedioxy-2,4,6-trimethyl-7- [(tert-butyl)-dimethylsilyloxy]non-1-yl phenyl sulfoxides (6), the condensation of which with (3R,4S,5R,6S)-7-benzyloxy-3,5-isopropylidenedioxy-4,6-dimethylheptan-2-o ne (7) led to the partially-protected seco-acid of the 9,12-anhydroerythronolide aglycon (5). (C) 1998 Elsevier Science Ltd. All rights reserved.

Keywords: antibiotics ; bicyclic heterocyclic compounds ; furans ; polyketides ; Polypropionate fragments ; erythronolide-b ; sporeamicin-a ; derivatives ; sequence

Note:

Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland.

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Record created on 2005-11-09, modified on 2012-03-20

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