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Communication | Regular issue | Vol 71, No. 10, 2007, pp.2113-2118
Published online, 10th July, 2007
DOI: 10.3987/COM-07-11119
First Total Syntheses of New Phenylpropanoid Lignans, (±)-Aglacin K Stereoisomer and (±)-Arborone

Masaki Takahashi, Koji Takada, Daisuke Matsuura, Kunihiko Takabe, and Hidemi Yoda*

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

Abstract

An efficient and convergent process is described for the first preparation of new phenylpropanoid lignans, (±)-aglacin K stereoisomer and (±)-arborone, isolated from the stem bark of Algaia cordata and the stems of Piper arborescens, respectively. The key substituted tetrahydrofuran rings were constructed through chemoselective hydrogenation of functionalized lactol derivatives, which were in turn elaborated via requisite reverse stereoselective addition of organometallic reagent to the amide-aldehyde intermediates derived from a terpene lactone.