Brevipolides are 5,6-dihydro-?-pyrone derivatives, isolated from Hyptis brevipesin 2009.1 These natural products exhibit cytotoxicity against MCF-7 human breast cancer cell line with ED50< 10 �M.1,2The structural features of brevipolides include the cyclopropyl ketone and coumarate, inaddition to the 5,6-dihydro-?-pyron. To date, their total synthesis has not been reported.We utilized C2 symmetric dienediol as the starting material, and the skeleton of brevipolides was prepared by diastereoselective cyclopropanation and ring-closing metathesis. The total synthesis was achieved after the formation of the coumaric ester and deprotection. The stereochemistry of the synthetic intermediate was confirmed by X-ray crystallography. References(1) Y. Deng, M. J. Balunas, J.-A. Kim, D. D. Lantvit, Y.-W. Chin, H. Chai, S. Sugiarso, L. B. S. Kardono, H. H. S. Fong, J. M. Pezzuto, S. M. Swanson, E. J. C. de Blanco, and A. D. Kinghorn J. Nat. Prod. 2009  , 72, 1165-1169.(2) G. A. Sua�rez-Ortiz, C. M. Cerda-Garc�a-Rojas, A. Herna�ndez-Rojas, and R. Pereda-Miranda J. Nat. Prod. 2013  , 76, 72-78.

Asymmetric synthesis of brevipolides

248th National Meeting (2014)

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