57371-44-5Relevant articles and documents
First Enantioselective Synthesis of Surinamensinol B and a Non-Natural Polysphorin Analogue by a Two-Stereocentered Hydrolytic Kinetic Resolution
Lalwani, Komal G.,Sudalai, Arumugam
, p. 7344 - 7351 (2015/11/25)
An efficient and economical approach to the synthesis of antitumor and anti-inflammatory surinamensinol B (1) and antimalarial polysphorin analogue 2 has been achieved with high enantiomeric purity (96 % ee) by starting from commercially available 3,4,5-trimethoxybenzaldehyde. The key steps of the strategy include a Co-catalyzed two-stereocentered hydrolytic kinetic resolution (HKR) of racemic 2-[(methoxymethoxy)(3,4,5-trimethoxyphenyl)methyl]oxirane (13) as the chiral inducing step followed by a Mitsunobu reaction. Chiral epoxide 14 and chiral diol 15 were utilized in the syntheses of both compounds.
The first stereoselective total synthesis of a new antitumour and anti-inflammatory neolignan, surinamensinol A
Reddy, Parigi Raghavendar,Das, Biswanath
, p. 7432 - 7434 (2014/02/14)
The stereoselective total synthesis of an antitumour and anti-inflammatory 8-O-4′-neolignan, surinamensinol A has been accomplished starting from two aldehydes, 3,4,5-trimethoxy benzaldehyde and vanillin. The key steps involve an asymmetric reduction using a chiral oxazaborolidine complex, a Sharpless asymmetric dihydroxyllation and a Mitsunobu reaction. This is the first report of the total synthesis of surinamensinol A.
Synthesis of gingerol and diarylheptanoids
Sabitha, Gowravaram,Srinivas, Chitti,Reddy, Teega Rammohan,Yadagiri, Kurra,Yadav, Jhillu Singh
experimental part, p. 2124 - 2133 (2012/03/27)
The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds.