Asymmetric synthesis of biologically useful 3,4-disubstitutedgamma- lactone (3,4-db).
3,4-Disubstituted gamma-lactones 9 and 10 were stereoselectively synthesized from 3,4-unsaturated aliphatic alcohol. The synthetic methods of homoallylic alcohol were discussed. Asymmetric dihydroxylation of the double bond was performed by Sharpless' method with (DHQD)2 PHAL or (DHQ)2 PHAL. The stereochemistry of the product was assigned. The (3R,4R)- and (3S,4S)-compounds were obtained with high enantiomeric excess.
Cheong
C S
CS
Life Sciences Division, Korea Institute of Science and Technology, P.O. BOX 131, Cheongryang, Seoul 130-650, Korea. c249@kist.re.kr
Park
Y J
YJ
Lee
S H
SH
Im
D S
DS
Jung
S H
SH
D000438:Alcohols / Q000737:chemistry*; D001230:Aspergillus / Q000737:chemistry* / Q000378:metabolism; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D005663:Furans; D007783:Lactones; C431664:Mer-WF5027