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Synlett 1998; 1998(10): 1132-1134
DOI: 10.1055/s-1998-1872
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Model Study of the Hoppe Reaction Between Racemic Titanated Crotyl Carbamate and Enantiopure Aldehyde or γ-Lactol

Isabelle Berque* , Patrick Le Ménez, Patrick Razon, Claude Anies, Ange Pancrazi, Janick Ardisson, Alain Neuman, Thierry Prangé, 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 our strategy for the total synthesis of tylonolide 2, aglycon of tylosin 1, and for the construction of the eastern part C1-C9, we planned to carry out a Hoppe homoaldolisation. In a model study, reaction was performed between racemic titanated crotyl carbamate (±)-3b and optically active aldehydes 6a-c. The expected syn-anti adducts 7a-c were obtained in good isolated yield together with the anti-anti isomer 8a-c. Interestingly, the γ-lactol 6d was also tested and delivered the syn-anti 7d compound in 70% isolated yield.

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