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The synthesis of stereoisomers of acuminatolide is rare and requires complex and time-consuming multistep procedures. Asarinin (1) and sesamin (2), two diasteromeric tetrahydrofurofuran lignans, are efficiently mono-dearylated by methyltrioxorhenium (MTO, I) and hydrogen peroxide (H2O2) or urea hydrogen peroxide adduct (UHP) as primary oxidant to give (-)-(7R,8'R,8R)-acuminatolide (3A) and (+)-(7S,8R,8'R)-acuminatolide (3B), respectively, in high yield and diastereoselectivity (de &gt;98%). The oxidation of 1 was also performed with novel heterogeneous catalysts based on the heterogenation of MTO on poly(4-vinylpyridine) and polystyrene resins. In these latter cases 3A was obtained with a different yield and selectivity depending on the physical-chemical properties of the support. Cytotoxic effects of 3A and 3B in mammalian cell lines in vitro are also reported.

journal of natural products

An Efficient and Stereoselective Dearylation of Asarinin and Sesamin Tetrahydrofurofuran Lignans to Acuminatolide by Methyltrioxorhenium/H<sub>2</sub>O<sub>2</sub> and UHP Systems

An Efficient and Stereoselective Dearylation of Asarinin and Sesamin Tetrahydrofurofuran Lignans to Acuminatolide by Methyltrioxorhenium/H2O2 and UHP Systems

An Efficient and Stereoselective Dearylation of Asarinin and Sesamin Tetrahydrofurofuran Lignans to Acuminatolide by Methyltrioxorhenium/H₂O₂ and UHP Systems