201049-10-7Relevant academic research and scientific papers
Bioinspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels-Alder Reaction, LiAlH4-Mediated Isomerization, and Acid-Mediated Cyclization
Songthammawat, Poramate,Wangngae, Sirilak,Matsumoto, Koki,Duangkamol, Chuthamat,Ruchirawat, Somsak,Ploypradith, Poonsakdi
, p. 5225 - 5241 (2018)
The cyclohexene moiety of the tricyclic 6,7-diaryl-tetrahydro-6H-benzo[c]chromene core of palodesangrens could be assembled in a biomimetic and step-economical fashion by the Diels-Alder reaction between the electron-rich (E)-1,3-butadienylarenes as the diene and the electron-deficient chalcones as the dienophile. During the reduction of ketone to the corresponding alcohol by LiAlH4, the mixture of endo and exo isomers underwent a novel diastereoconvergent LiAlH4-mediated isomerization to install the desired stereochemistry at C10a. Subsequent pyran ring closure under acidic conditions installed the stereochemistry at the remaining C6. Overall, the tricyclic core of palodesangrens could be prepared in three steps and up to 38% yield.
Enantioselective synthesis of flavonoids. Part 3. trans- and cis-flavan-3-ol methyl ether acetates
Van Rensburg, Hendrik,Van Heerden, Pieter S.,Ferreira, Daneel
, p. 3415 - 3421 (2007/10/03)
Asymmetric dihydroxylation of a series of polyoxygenated 1,3-diarylpropenes with AD-mix-α or AD-mix-β in the presence of methanesulfonamide and subsequent acid-catalysed cyclization, affords for the first time synthetic access to trans- and cis-flavan-3-ol derivatives, essentially enantiopure and in good yield.
