A new approach for the asymmetric total synthesis of umbelactone.
The asymmetric total syntheses of (R)-(+)- and (S)-(-)-umbelactone were achieved by using the Sharpless asymmetric epoxidation reaction to generate the stereogenic center and a ring-closing metathesis (RCM) for the formation of the lactone structure. Starting from 3-methyl-2-buten-1-ol, the asymmetric total synthesis was achieved in an efficient 6-step protocol with an overall yield of 16%.
Liu
Huawei
H
State Key Laboratory of Applied Organic Chemistry, Institute of Organic Chemistry, Lanzhou University, Lanzhou, PR China.
Zhang
Tao
T
Li
Yulin
Y
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D045782:Hemiterpenes; D007202:Indicators and Reagents; D007783:Lactones / Q000032:analysis / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D000439:Pentanols / Q000737:chemistry; D013237:Stereoisomerism
D045782:Hemiterpenes; D007202:Indicators and Reagents; D007783:Lactones; D000439:Pentanols; C009034:prenol