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Synlett 1998; 1998(10): 1135-1137
DOI: 10.1055/s-1998-1873
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Enantioselective Synthesis of a C1-C9 Moiety of Tylonolide, Tylosin Aglycon

Isabelle Berque* , Patrick Le Ménez, Patrick Razon, Ange Pancrazi, Janick Ardisson, Jean-Daniel Brion
  • *Laboratoire de Chimie Thérapeutique, URA 1843 BIOCIS, Faculté de Pharmacie, 92296, Châtenay-Malabry, France
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Publication Date:
31 December 2000 (online)

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In an approach to the C1-C9 eastern part 2 of tylonolide, aglycon of tylosin 1, an extension of the Hoppe reaction was, in a first key step, carried out between carbamate 6 and optically active aldehyde 5a and γ-lactol 5b. The latter gave the expected 7b adduct in 85% yield. After a homologation sequence, the C1-C7 fragment 14b was prepared and submitted to a second allylation reaction with crotyl N,N-diisopropyl carbamate to deliver compound 16 in 80% yield as a C1-C9 moiety of tylonolide.

allyltitanate - Hoppe reaction - tylosin - homoaldolisation - γ-lactol

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