Enantioselective Synthesis of Cuparane Sesquiterpenes. Synthesis of (-)-Cuparene and (-)-δ-Cuparenol

…, C Agulló, M Arnó, AC Cunat, MT García…

Index: Abad, Antonio; Agullo, Consuelo; Arno, Manuel; Cunat, Ana C.; Garcia, M. Teresa; Zaragoza, Ramon J. Journal of Organic Chemistry, 1996 , vol. 61, # 17 p. 5916 - 5919

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Citation Number: 28

Abstract

(-)-Cuparene and (-)-δ-cuparenol, two cuparane-type sesquiterpenoids, were synthesized from β-cyclogeraniol in 47% and 27% overall yield, respectively, using a Katsuki-Sharpless asymmetric epoxidation, a pinacollic rearrangement, and a Robinson annulation as key synthetic steps.

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