171030-06-1Relevant articles and documents
Asymmetric protected enoates as key intermediates towards an EPC synthesis of (+)-heptelidic acid
Riehs, Gerhard,Urban, Ernst
, p. 7233 - 7234 (1995)
Conjugate addition of (H2C=CH)2CuLi to 6n and 7n gave the adducts 9n (5′R,6′R) and 10n (5′S,6′R) as single diastereomers, respectively. Finally, the (5′R) configurated enoate 6n turned out to be valuable as a chiral building block fo
EPC Synthesis of (+)-Heptelidic Acid
Riehs,Urban
, p. 281 - 289 (2007/10/03)
An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which g
Asymmetric protected 2-oxo-5-isopropyl-cyclohexenecarboxylates as key intermediates towards an EPC synthesis of (+)-heptelidic acids
Riehs,Urban
, p. 1221 - 1230 (2007/10/03)
Asymmetric shielded 2-oxo-5-isopropyl-cyclohexenecarboxylates 3n and 4n which are diastereomers at C-5' have been prepared by a five step synthesis and separated by chromatography. Conjugate addition of (H2C=CH)2CuLi to 3n and 4n gave the adducts 13n (5'R,6'R) and 14n (5'S,6'R) as single diastereomers, respectively. Finally, the (5'R) configurated enoate 3n turned out to be valuable as chiral building block for an EPC synthesis of (+)-heptelidic acid.