TY - JOUR
T1 - An efficient enantioselective synthesis of argentilactone
AU - Ramachandran, P. Veeraraghavan
AU - Reddy, M. Venkat Ram
AU - Brown, Herbert C.
PY - 1999/11/1
Y1 - 1999/11/1
N2 - Asymmetric allylboration of 2-octynal with (+)-B-allyldiisopinocampheylborane provides the corresponding homoallylic alcohol in 80% yield. The alkynenol is stereoselectively hydrogenated in the presence of Lindlar catalyst, converted to the corresponding acrylic ester, and cyclized by refluxing in dichloromethane in the presence of 10 mol% of Grubbs' catalyst to provide the natural enantiomer of (R)-(-)-argentilactone in 44% overall yield.
AB - Asymmetric allylboration of 2-octynal with (+)-B-allyldiisopinocampheylborane provides the corresponding homoallylic alcohol in 80% yield. The alkynenol is stereoselectively hydrogenated in the presence of Lindlar catalyst, converted to the corresponding acrylic ester, and cyclized by refluxing in dichloromethane in the presence of 10 mol% of Grubbs' catalyst to provide the natural enantiomer of (R)-(-)-argentilactone in 44% overall yield.
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M3 - Article
AN - SCOPUS:21044453937
SN - 0019-4522
VL - 76
SP - 739
EP - 742
JO - Journal of the Indian Chemical Society
JF - Journal of the Indian Chemical Society
IS - 11-12
ER -