Total Synthesis of (+)-Lophirone H and Its Pentamethyl Ether Utilizing an Oxonium-Prins Cyclization

Hossay Abas; Sean M Linsdall; Mathias Mamboury; Henry S Rzepa; Alan C Spivey

doi:10.1021/acs.orglett.7b00642

Total Synthesis of (+)-Lophirone H and Its Pentamethyl Ether Utilizing an Oxonium-Prins Cyclization

Org Lett. 2017 May 19;19(10):2486-2489. doi: 10.1021/acs.orglett.7b00642. Epub 2017 May 5.

Authors

Hossay Abas¹, Sean M Linsdall¹, Mathias Mamboury¹, Henry S Rzepa¹, Alan C Spivey¹

Affiliation

¹ Department of Chemistry, Imperial College London , South Kensington, London SW7 2AZ, U.K.

PMID: 28475343
DOI: 10.1021/acs.orglett.7b00642

Abstract

The first total synthesis of (+)-lophirone H (1) and its pentamethyl ether 29, featuring an oxonium-Prins cyclization/benzylic cation trapping reaction, is described.