802622-25-9Relevant academic research and scientific papers
The first catalytic asymmetric total synthesis of ent-hyperforin
Shimizu, Yohei,Shi, Shi-Liang,Usuda, Hiroyuki,Kanai, Motomu,Shibasaki, Masakatsu
experimental part, p. 6569 - 6584 (2010/10/19)
The first catalytic asymmetric total synthesis of ent-hyperforin was described here in detail. Keys to the success were a catalytic asymmetric Diels-Alder reaction, a stereoselective Clasien rearrangement, an intramolecular aldol cyclization, and a vinylogous Pummerer rearrangement. Along with the successful synthetic route, several attempted approaches toward the construction of bicyclo[3.3.1] core and the C2 oxidation were discussed.
Challenge toward structural complexity using asymmetric catalysis: Target-oriented development of catalytic enantioselective Diels-Alder reaction
Usuda, Hiroyuki,Kuramochi, Akiyoshi,Kanai, Motomu,Shibasaki, Masakatsu
, p. 4387 - 4390 (2007/10/03)
(Chemical Equation Presented) A new method for the catalytic enantioselective Diels-Alder reaction using polysubstituted silyl enol ethers as dienes is described. High enantioselectivity (up to 92% ee) was produced using a catalyst generated from FeBr3 and AgSbF6 in a 1:2 ratio and aryl-pybox (aryl = Ph or p-ethoxyphenyl). This reaction should facilitate the enantioselective synthesis of polycyclic acylphloroglucinols such as hyperforin or garsubellin A, which are currently of interest from synthetic and medicinal points of view.
