Total Synthesis of (+)-Lophirone H and its Pentamethylether Utilizing an Oxonium-Prins Cyclisation
Created: 2016-04-27 07:51
Last modified: 2017-05-26 09:45
The first total synthesis of (+)-lophirone H (1) and its pentamethylether derivative, featuring an oxonium-Prins cyclisation/benzylic cation trapping reaction, is described. This key step allows for the formation of all four stereocentres of the cis-fused 4H-furo[3,2-c]benzopyran core. Enantioselective preparation of the homoallylic alcohol Prins substrate is via an Evans-type asymmetric aldol/Heck reaction sequence.
|10.14469/hpc/2014||Computation data for Total Synthesis of (+)-Lophirone H and its Pentamethylether Utilizing an Oxonium-Prins Cyclisation|
|10.14469/hpc/2017||NMR data for Total Synthesis of (+)-Lophirone H and its Pentamethylether Utilizing an Oxonium-Prins Cyclisation|
|10.1021/acs.joc.5b01641||Synthesis of Furo[3,2-c]benzopyrans via an Intramolecular [4 + 2] Cycloaddition Reaction of o-Quinonemethides|
|10.1021/ol9024259||Stereoselective Synthesis of cis-2,3-Disubstituted Tetrahydrofurans via Oxonium-Prins Cyclization - Access to the Cordigol Ring System|