Enzymatic approach to enantiomerically pure 5-alken-2,4-diols and 4-hydroxy-5-alken-2-ones: application to the synthesis of chiral synthons.
Enantiomerically pure 1,3-diols 1-3 were obtained by a chemoenzymatic approach (lipase PS from Burkholderia cepacia). These diols were converted into useful chiral synthons, which could be considered homologues of glyceraldehyde and glyceric acid acetonides. Applications of these synthons to the de novo synthesis of sugars and preparation of conagenin carboxylic moiety were shown. Hydroxy ketone 4 was chosen as a model system for another synthetic evolution: it was obtained in enantiomerically pure form by enzymatic resolution and converted into chiral tetrahydropyranes, such as the stereoisomers of the commercial fragrance Gyrane.
Abate
Agnese
A
Dipartimento di Chimica, Materiali ed Ingegneria Chimica del Politecnico, CNR-Istituto del Riconoscimento Molecolare, Via Mancinelli 7, I-20131 Milan, Italy.
Brenna
Elisabetta
E
Costantini
Alessia
A
Fuganti
Claudio
C
Gatti
Francesco G
FG
Malpezzi
Luciana
L
Serra
Stefano
S
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D016956:Burkholderia cepacia / Q000201:enzymology; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005985:Glyceraldehyde / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D004952:Esters; D007659:Ketones; D005985:Glyceraldehyde; D008049:Lipase