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Note | Regular issue | Vol 53, No. 11, 2000, pp.2553-2560
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9015
Conjugate Addition of Arylmetal Reagents to an α,β-Unsaturated Ketone. Short Syntheses of (-)-Agatharesinol Dimethyl Ether and (-)-Sugiresinol Dimethyl Ether

Keizo Matsuo,* Yuji Ono, Atsutaka Seki, Hiroshi Kuwajima, and Keiji Nishiwaki

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka, Osaka 577-8502, Japan

Abstract

(-)-Agatharesinol dimethyl ether and (-)-sugiresinol dimethyl ether, derivatives of (-)-agatharesinol and (-)-sugiresinol isolated from Agathis australisand Cryptomeria japonica, respectively were synthesized starting from aprotected D-glyceraldehyde in five steps through 1,4-conjugate addition of arylmetal reagents to an α,β-unsaturated ketone.