Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 21, Pages 10722-10726Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502139m
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Funding
- Process Chemistry Division, H. Lundbeck A/S, Copenhagen, Denmark
- Mark A. Nordenberg Chancellor's Distinguished Teaching Award from the University of Pittsburgh
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Concise syntheses of the sesquiterpenes (R)-(+)-cuparene and (R)-(+)-herbertene by asymmetric cyclization of achiral olefinic alkyllithium precursors in the presence of (-)-sparteine are reported. The quaternary stereogenic center in each product is set at the final step of the synthesis by enantioselective (er = 61:39) 5-exo ring closure.
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