The first asymmetric total syntheses and determination of absolute configurations of xestodecalactones B and C.
The first efficient asymmetric total syntheses of xestodecalactones B and C have been accomplished in 10 steps with an overall yield of 22 and 20.2%, respectively. The key steps involve the utility of Evans oxazolidinone-mediated syn-aldol condensations to establish the C-9 configuration and the macrolide ring formation by intramolecular acylation. The absolute configurations of xestodecalactones B and C have been determined via these syntheses.
Liang
Qiren
Q
Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P.R. China.
Zhang
Jiyong
J
Quan
Weiguo
W
Sun
Yongquan
Y
She
Xuegong
X
Pan
Xinfu
X
D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; C471497:xestodecalactone B; C471498:xestodecalactone C