Total Synthesis of (+)-Lophirone H and its Pentamethylether Utilizing an Oxonium-Prins Cyclisation

DOI: 10.14469/hpc/436 Metadata

Created: 2016-04-27 07:51

Last modified: 2017-05-26 09:45

Author: Henry Rzepa

Co-author: Alan Spivey
Co-author: Hossay Abas
Co-author: Sean Linsdall
Co-author: Hossay Abas
Co-author: Mathias Mamboury

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.

Members

DOIDescription
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

Associated DOIs

DOIDescription
10.1021/acs.joc.5b01641 Synthesis of Furo[3,2-c]benzopyrans via an Intramolecular [4 + 2] Cycloaddition Reaction of o-Quinonemethides
10.1021/acs.orglett.7b00642 Published article
10.1021/ol9024259 Stereoselective Synthesis of cis-2,3-Disubstituted Tetrahydrofurans via Oxonium-Prins Cyclization - Access to the Cordigol Ring System

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