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Enantioselective Synthesis of a Furan Lignan (+)-Sylvone
Eunhye Lee1, Jiyun Bang1, Jisook Kwon1
1Department of Chemistry, Sungkyunkwan University , Suwon 440-746, Korea.
Abstract:
A synthesis of natural tetrahydrofuran lignan (+)-sylvone is achieved starting from methyl allenoate in 5 steps. The synthesis begins from an enantioselective aldol reaction of methyl allenoate with 3,4-dimethoxybenzaldehyde to afford α-addition aldol adduct. Key steps for the synthesis of sylvone include an oxacyclization of the α-hydroxy allenyl adduct followed by a Michael addition of a 1,3-dithiane derivative to establish a sylvone skeleton with suitable stereoselections.
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