1235485-64-9Relevant academic research and scientific papers
Harnessing the Power of the Asymmetric Grignard Synthesis of Tertiary Alcohols: Ligand Development and Improved Scope Exemplified by One-Step Gossonorol Synthesis
Gilheany, Declan G.,Kavanagh, Saranna E.
supporting information, p. 8198 - 8203 (2020/11/18)
A series of N-substituted cyclohexyldiaminophenolic ligands for the asymmetric Grignard synthesis of tertiary alcohols is reported. The 2,5-dimethylpyrrole-decorated ligand led to improved enantioselectivities and broadened the scope of the methodology. As an exemplar, we report an unprecedented highly selective one-step synthesis of gossonorol in 93% ee, also constituting the shortest formal syntheses of natural products boivinianin B and yingzhaosu C.
Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes
Aggarwal, Varinder K.,Ball, Liam T.,Carobene, Simon,Connelly, Rickki L.,Hesse, Matthew J.,Partridge, Benjamin M.,Roth, Philippe,Thomas, Stephen P.,Webster, Matthew P.
supporting information; experimental part, p. 9230 - 9232 (2012/09/10)
The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in few
Enantioselective synthesis of (+)-gossonorol and related systems using organozinc reagents
Gonzalez-Lopez, Susana,Yus, Miguel,Ramon, Diego J.
, p. 611 - 615 (2012/08/13)
The sesquiterpene (+)-gossonorol is prepared in only three synthetic steps in 60% overall yield and 82% ee from commercially available reagents. The key asymmetric step is the catalytic enantioselective addition of dimethylzinc to 5-methyl-1-(2-methylphen
Synthesis of (+)- and (-)-gossonorol and cyclisation to boivinianin B
Abecassis, Keren,Gibson, Susan E.
experimental part, p. 2938 - 2944 (2010/08/07)
The first enantioselective synthesis of gossonorol has been achieved in good overall yield and excellent enantioselectivity, demonstrating the utility of a novel approach to enantiopure tertiary benzylic alcohols. Epoxidation of enantiopure gossonorol followed by acid-catalysed cyclisation gave a diastereoisomeric mixture of boivinianin B, typical of the diastereoisomeric mixtures of this compound found in nature. Separation of the diastereoisomers and determination of their enantiopurity revealed that the stereochemical integrity of the benzylic alcohol of gossonorol had been preserved during the epoxidation/cyclisation reaction.
