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Communication | Regular issue | Vol 65, No. 3, 2005, pp.519-522
Published online, 21st January, 2005
DOI: 10.3987/COM-04-10296
A New Synthetic Entry to Furofuranoid Lignans, Methyl Piperitol and Fargesin

Hidemi Yoda,* Yuji Suzuki, Daisuke Matsuura, and Kunihiko Takabe

*Department of Molecular Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan

Abstract

An efficient and general process is described for the preparation of the unsymmetrically substituted diequatorial and axial-equatorial furofuran lignans, methyl piperitol and fargesin. The synthetic strategy is based on a stereoselective manner by nucleophilic addition of organometallic reagent to the monoterpene lactone elaborated from dihydroxyacetone dimer followed by condensation with the corresponding aromatic aldehyde counter part.