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 > 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.

Saladino, R., Fiani, C., Crestini, C., Argyropoulos, D., Marini, S., Coletta, M. (2007). An efficient and stereoselective dearylation of asarinin and sesamin tetrahydrofurofuran lignans to acuminatolide by methyltrioxorhenium/H2O2 and UHP systems. JOURNAL OF NATURAL PRODUCTS, 70(1), 39-42 [10.1021/np060479u].

An efficient and stereoselective dearylation of asarinin and sesamin tetrahydrofurofuran lignans to acuminatolide by methyltrioxorhenium/H2O2 and UHP systems

CRESTINI, CLAUDIA;MARINI, STEFANO;COLETTA, MASSIMILIANO
2007-01-01

Abstract

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 > 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.
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/03 - Chimica Generale e Inorganica
English
Con Impact Factor ISI
acuminatolide; asarinin; hydrogen peroxide; lignan derivative; methyltrioxorhenium; rhenium; sesamin; sesamin tetrahydrofurofuran lignan derivative; animal cell; article; arylation; controlled study; cytotoxicity; drug structure; drug synthesis; in vitro study; mammal cell; nonhuman; stereochemistry; Animals; Antineoplastic Agents; Dioxoles; Drug Screening Assays, Antitumor; Humans; Lignans; Mice; Molecular Structure; Organometallic Compounds; Oxidation-Reduction; Rhenium; Stereoisomerism; Zanthoxylum; Mammalia
Saladino, R., Fiani, C., Crestini, C., Argyropoulos, D., Marini, S., Coletta, M. (2007). An efficient and stereoselective dearylation of asarinin and sesamin tetrahydrofurofuran lignans to acuminatolide by methyltrioxorhenium/H2O2 and UHP systems. JOURNAL OF NATURAL PRODUCTS, 70(1), 39-42 [10.1021/np060479u].
Saladino, R; Fiani, C; Crestini, C; Argyropoulos, D; Marini, S; Coletta, M
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/34755
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