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The stereoselective total synthesis of (−)-12,13-epi-obtusenyne is described. The oxonene skeleton possessing cis-orientated alkyl substituents at the α,α′-positions to ether linkage was stereoselectively constructed via cyclization of the corresponding hydroxy epoxide promoted by Eu(fod)3.

Other natural products U 0800Total Synthesis of (-)-12,13-epi-Obtusenyne. -The oxonene skeleton of the title compound (III) possessing cis-orientated alkyl substituents at the α,α'-position to ether linkage is stereoselectively constructed via cyclization of the corresponding hydroxy epoxide (I). -(SUZUKI*, T.; YOSHINO, N.; UEMURA, T.; HAGIWARA, H.; HOSHI, T.; Chem. Lett. 36 (2007) 2, 278-279; Fac. Eng., Niigata Univ., Ikarashi, Niigata 950-21, Japan; Eng.) -H. Toeppel 28-184