1430737-52-2Relevant academic research and scientific papers
General methodologies toward cis-fused quinone sesquiterpenoids. enantiospecific synthesis of the epi-Ilimaquinone core featuring Sc-catalyzed ring expansion
Kaplan, Hilan Z.,Rendina, Victor L.,Kingsbury, Jason S.
, (2017)
A stereocontrolled approach to the cis-decalin framework of clerodane diterpenes and biologically active quinone sesquiterpenes is reported. Starting from an inexpensive optically pure tetrahydroindanone, Birch reductive alkylation builds two new contiguous chiral centers—one of which is quaternary and all-carbon-substituted. Also featured is a highly regioselective diazoalkane—carbonyl homologation reaction to prepare the 6,6-bicyclic skeleton. Therein, the utility of Sc(OTf)3 as a mild catalyst for formal 1C insertion in complex settings is demonstrated.
Diastereoselective synthesis of complex cis-hexahydroindanes by reductive alkylation
Kaplan, Hilan Z.,Rendina, Victor L.,Kingsbury, Jason S.
, p. 4620 - 4626 (2013/06/27)
An efficient and operationally simple approach to complex cis-hexahydroindanes is reported. Upon Birch reduction of unprotected, C4-alkylated tetrahydroindanols and electrophilic trapping of the tetrasubstituted enolate, cis-fused products are formed with a new stereogenic quaternary carbon. The reaction is convergent, completely diastereoselective, and shows a broad scope with regard to the electrophile.
