91364-47-5Relevant academic research and scientific papers
Total Synthesis of (±)-Englerin A and Its Tuncated Analogues
Reagan, Colleen,Trevitt, Graham,Tchabanenko, Kirill
, p. 1027 - 1037 (2019)
A convergent approach allowed total synthesis of (±)-Englerin A, and its truncated analogues, employing a thermal 1,3-dipolar cycloaddition of a highly substituted pyrylium ylide with vinyl acetate as the key step. The key intermediate, a 8-oxabicyclo[3,2,1]octane oxygenated at the C6 position, was directly converted into a truncated Englerin A analogue. CuI catalyzed conjugate addition of vinyl Grignard to an enone, ozonolysis, and epimerisation of the resulting aldehyde allowed stereoselective introduction of the side-chain leading to a total synthesis of the racemic natural product. The developed chemistry will allow synthesis of more complex analogues of the natural product based on the use of the key bicyclo[3,2,1]octane scaffold.
A brief synthesis of (-)-englerin A
Li, Zhenwu,Nakashige, Mika,Chain, William J.
supporting information; experimental part, p. 6553 - 6556 (2011/06/22)
Englerins A and B are guaiane sesquiterpenes that were isolated from the bark of Phyllanthus engleri, a plant indigenous to east Africa. The englerins consist of a 5-6-5 fused tricyclic structure with an ether bridge and two ester-bearing stereogenic cent
