Asymmetric synthesis of umuravumbolide.
[figure: see text] This first asymmetric synthesis of enantiopure desacetylumuravumbolide and umuravumbolide via asymmetric reduction, allylboration, and ring-closing metathesis confirms their revised structures and configurations. A convenient procedure to upgrade the enantiopurity of alpha,beta-acetylenic alcohols is also described.
Reddy
M V
MV
Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA.
Rearick
J P
JP
Hoch
N
N
Ramachandran
P V
PV
D002384:Catalysis; D019686:Lamiaceae; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010946:Plants, Medicinal; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011753:Pyrones; C430366:desacetylumuravumbolide; C430365:umuravumbolide