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.

A Short, Protecting Group-Free Total Synthesis of Bruceollines D, E, and J. -(LOPCHUK, J. M.; GREEN, I. L.; BADENOCK, J. C.; GRIBBLE*, G. W.; Org. Lett. 15 (2013) 17, 4485-4487, http://dx.doi.org/10.1021/ol402042f ; Dep. Chem., Dartmouth Coll., Hanover, NH 03755, USA; Eng.) -Mais 01-227