MODEL STUDY OF THE HOPPE REACTION BETWEEN RACEMIC TITANATED CROTYL CARBAMATE AND ENANTIOPURE ALDEHYDE OR GAMMA-LACTOL

Authors
BERQUE I LEMENEZ P RAZON P ANIES C PANCRAZI A ARDISSON J NEUMAN A PRANGE T BRION JD
Citation
I. Berque et al., MODEL STUDY OF THE HOPPE REACTION BETWEEN RACEMIC TITANATED CROTYL CARBAMATE AND ENANTIOPURE ALDEHYDE OR GAMMA-LACTOL, Synlett, (10), 1998, pp. 1132
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
10
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):10<1132:MSOTHR>2.0.ZU;2-6
Abstract
In our strategy for the total synthesis of tylonolide 2, aglycon of ty losin 1, and for the construction of the eastern part C1-C9, we planne d to carry out a Hoppe homoaldolisation. In a model study, reaction wa s performed between racemic titanated crotyl carbamate (+/-)-3b and op tically 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 gamma-lactol 6d was also tested and delivered t he syn-anti 7d compound in 70% isolated yield.