J. Lopchuk, Ilene L. Green, Jeanese C. Badenock
Aug 12, 2013
Citations
0
Influential Citations
22
Citations
Journal
Organic letters
Abstract
A short, protecting group-free total synthesis of bruceollines D, E, and J has been achieved. The enantioselective reduction of bruceolline E with β-chlorodiisopinocampheylborane delivers both the natural and unnatural enantiomers of bruceolline J in excellent yields and enantioselectivities. Reduction with baker's yeast and sucrose was shown to provide the unnatural enantiomer of bruceolline J in 98% ee.