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

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An efficient and stereoselective dearylation of asarinin and sesamin tetrahydrofurofuran lignans to acuminatolide by methyltrioxorhenium/H(2)O(2) and UHP systems.

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 (+)-...

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ژورنال

عنوان ژورنال: Journal of Natural Products

سال: 2007

ISSN: 0163-3864,1520-6025

DOI: 10.1021/np060479u