928780-23-8

Basic information

• Product Name: (-)-(7R,8R,8'R)-acuminatolide
• CAS NO: 928780-23-8
• Molecular Weight: 248.235
• Mol File: 928780-23-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (-)-(7R,8R,8'R)-acuminatolide(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(7R,8R,8'R)-acuminatolide(928780-23-8)
• EPA Substance Registry System: (-)-(7R,8R,8'R)-acuminatolide(928780-23-8)

Safety Data

• Hazardous Substances Data: 928780-23-8(Hazardous Substances Data)

Upstream product

• 133-04-0 episesamin 

Relevant articles and documents

An efficient and stereoselective dearylation of asarinin and sesamin tetrahydrofurofuran lignans to acuminatolide by methyltrioxorhenium/H 2O2 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 (H2O 2) 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.