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Synlett 1991; 1991(9): 611-614
DOI: 10.1055/s-1991-20814
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Synthesis of the C10-C25 Northern Moiety of 22,23-Dihydroavermectin B1b

Jean Pierre Férézou* , Marc Julia, Rami Khourzom, Ange Pancrazi, Pierre Robert
  • *Laboratoire de Chimie, École Normale Supérieure, 24 rue Lhomond F-75231 Paris Cedex 05, France
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Publication Date:
07 March 2002 (online)

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The C10-C25 spiroacetal moiety of 22,23-dihydroavermectin B1b aglycone has been prepared starting from a previously described optically active C15-C25 sulfone precursor. An asymmetric Hoppe's homoaldol reaction between the intermediate C13-C25 unsaturated aldehyde and enantiomerically enriched titanium (E)-2-butenyl N,N-diisopropylcarbamate, obtained in the presence of (-)-sparteine and tetra(isopropoxy)titanium, generates an anti 12S,13S C10-C25 vinyl carbamate which was transformed into the E-vinylstannane required for the coupling reaction with the C1-C9 part of avermectins.

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