10.14469/HPC/436
Rzepa, Henry
Henry
Rzepa
https://orcid.org/0000-0002-8635-8390
Imperial College London
Total Synthesis of (+)-Lophirone H and its Pentamethylether Utilizing an Oxonium-Prins Cyclisation
Imperial College London
2016
Results
Imperial College London
Imperial College Research Computing Service
Rzepa, Henry
Henry
Rzepa
https://orcid.org/0000-0002-8635-8390
Imperial College London
Abas, Hossay
Hossay
Abas
https://orcid.org/0000-0003-2922-1539
Imperial College London
Spivey, Alan
Alan
Spivey
https://orcid.org/0000-0001-5114-490X
Imperial College London
Linsdall, Sean
Sean
Linsdall
https://orcid.org/0000-0003-3798-769X
Imperial College London
Abas, Hossay
Hossay
Abas
https://orcid.org/0000-0003-2922-1539
Mamboury, Mathias
Mathias
Mamboury
https://orcid.org/0000-0002-7405-0639
2016
https://data.hpc.imperial.ac.uk/resolve/?ore=436
10.1021/acs.joc.5b01641
10.1021/acs.orglett.7b00642
10.1021/ol9024259
10.14469/hpc/2017
10.14469/hpc/2014
Creative Commons: Public Domain Dedication 1.0
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. Full NMR data is available.