Download PDF
Synlett 1991; 1991(9): 611-614
DOI: 10.1055/s-1991-20814
letter
© 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.

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
Further Information

Publication History

Publication Date:
07 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.