835922-48-0Relevant academic research and scientific papers
Concise access toward chiral hydroxy phenylpropanoids: formal synthesis of virolongin B; kigelin; kurasoin A; 4-hydroxysattabacin, and actinopolymorphol A
Patil, Sagar N.,Tilve, Santosh G.
, p. 3371 - 3375 (2016/07/11)
A simple, two step strategy consisting of Sharpless asymmetric dihydroxylation followed by regioselective breaking of [Formula presented] bond is utilized to target key chiral intermediates of natural products virolongin B, kigelin, kurasoin A, 4-hydroxy-sattabacin, and actinopolymorphol A. Derivatives of enantiopure hydroxy phenyl propanoids and α-hydroxy Weinreb amides are synthesized. The reductive cleavage of [Formula presented] bond in a regioselective manner is obtained using Pd/C in methanol.
Chemoenzymatic synthesis of enantiomerically pure syn-configured 1-aryl-3-methylisochroman derivatives
Simon, Robert C.,Busto, Eduardo,Richter, Nina,Belaj, Ferdinand,Kroutil, Wolfgang
supporting information, p. 111 - 121 (2014/01/06)
A two-step synthesis of various enantiomerically pure 1-aryl-3- methylisochroman derivatives was accomplished through asymmetric biocatalytic ketone reduction followed by an oxa-Pictet-Spengler reaction. The compounds were obtained in good to excellent yield (47-92 %) in favor of the syn diastereomers [dr (syn/anti) up to 99:1]. Enantiopure arylpropanols serving as pronucleophiles for the C-C bond-formation step were obtained by biocatalytic reduction by employing enantiocomplementary alcohol dehydrogenases, which gave access to the (S) and (R) enantiomer with up to >99 % conversion and up to >99 % ee. A two-step sequence involving a biocatalytic hydrogen-transfer reduction and a syn-diastereoselective oxa-Pictet-Spengler reaction was established to provide a series of 1-aryl-3-methylchroman derivatives with perfect enantioselectivity; PTSA = para-toluenesulfonic acid. Copyright
First enantioselective synthesis of the neolignans Rhaphidecursinol A and Virolongin B
Ren, Xinfeng,She, Xuegong,Peng, Kun,Su, Ying,Xie, Xingang,Pan, Xinfu,Zhang, Hongbin
, p. 969 - 974 (2007/10/03)
The enantioselective synthesis of the neolignans Rhaphidecursinol A and Virolongin B is reported for the first time. The key reactions in the synthesis were Sharpless asymmetric dihydroxylation and Mitsunobu reaction. The absolute configuration of Rhaphidecursinol A was confirmed.
