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: 2020-06-01 17:14
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: Alan Spivey Co-author: Hossay Abas Co-author: Sean Linsdall Co-author: Hossay Abas Co-author: Mathias Mamboury
Description
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.
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/2017 | NMR data for Total Synthesis of (+)-Lophirone H and its Pentamethylether Utilizing an Oxonium-Prins Cyclisation |
| 10.14469/hpc/2014 | Computation data for Total Synthesis of (+)-Lophirone H and its Pentamethylether Utilizing an Oxonium-Prins Cyclisation |
Associated DOIs
| Current dataset ... | DOI | Description |
|---|---|---|
| References | 10.1021/acs.joc.5b01641 | Published article: Synthesis of Furo[3,2-c]benzopyrans via an Intramolecular [4 + 2] Cycloaddition Reaction of o-Quinonemethides |
| References | 10.1021/acs.orglett.7b00642 | Published article: Total Synthesis of (+)-Lophirone H and Its Pentamethyl Ether Utilizing an Oxonium–Prins Cyclization |
| References | 10.1021/ol9024259 | Published article: Stereoselective Synthesis of cis-2,3-Disubstituted Tetrahydrofurans via Oxonium-Prins Cyclization - Access to the Cordigol Ring System |