A concise route for the synthesis of tetracyclic meroterpenoids: (±)-aureol preparation and mechanistic interpretation

2026-04-27T12:26:34Zhttps://uvadoc.uva.es/oai/request

oai:uvadoc.uva.es:10324/589782023-03-20T20:00:28Zcom_10324_1148com_10324_931com_10324_894col_10324_1270

A concise route for the synthesis of tetracyclic meroterpenoids: (±)-aureol preparation and mechanistic interpretation Rosales Martínez, Antonio Enríquez Giraudo, María Lourdes Jaraíz Maldonado, Martín Pozo Morales, Laura Rodríguez García, Ignacio Díaz Ojeda, Emilio Natural products - Synthesis Productos naturales Química orgánica - Síntesis Producción Científica A new concise general methodology for the synthesis of different tetracyclic meroterpenoids is reported: (±)-aureol (1), the key intermediate of this general route. The synthesis of (±)-aureol (1) was achieved in seven steps (28% overall yield) from (±)-albicanol. The key steps of this route include a C–C bond-forming reaction between (±)-albicanal and a lithiated arene unit and a rearrangement involving 1,2-hydride and 1,2-methyl shifts promoted by BF3•Et2O as activator and water as initiator. 2023-03-20 2023-03-20 2020 info:eu-repo/semantics/article Marine Drugs, 2020, Vol. 18, Nº. 9, 441 1660-3397 https://uvadoc.uva.es/handle/10324/58978 10.3390/md18090441 441 9 Marine Drugs 18 1660-3397 eng https://www.mdpi.com/1660-3397/18/9/441 info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/4.0/ © 2020 The Authors Atribución 4.0 Internacional MDPI