Journal
ORGANIC LETTERS
Volume 15, Issue 17, Pages 4485-4487Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol402042f
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- Department of Education GAANN fellowship
- Donors of the Petroleum Research Fund (PRF)
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A short, protecting group-free total synthesis of bruceollines D, E, and J has been achieved. The enantioselective reduction of bruceolline E with beta-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.
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