A short, protecting group-free total synthesis of bruceollines D, E, and J.
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.
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
Justin M
JM
Lopchuk
Ilene L
IL
Green
Jeanese C
JC
Badenock
Gordon W
GW
Gribble
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D032269:Brucea / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012441:Saccharomyces cerevisiae / Q000737:chemistry; D013237:Stereoisomerism; D013395:Sucrose / Q000737:chemistry
D001688:Biological Products; D006575:Heterocyclic Compounds, 3-Ring; C586355:bruceolline D; C586356:bruceolline E; C586357:bruceolline J; D013395:Sucrose