Structure and Computational Basis for Backbone Rearrangement in Marine Oxasqualenoids

Six novel oxasqualenoids (polyether triterpenes) were isolated from the red alga Laurencia viridis. Laurokanols A–E (1–5) comprise an unreported tricyclic core with a [6,6]-spiroketal system. Yucatecone (6) shows a biogenetically intriguing epimerization at C14. Quantum mechanical calculations were...

Descripción completa

Detalles Bibliográficos
Autores: Cen-Pacheco, Francisco, Santiago-Benítez, Adrián J., Tsui, Ka Yi, Tantillo, Dean J., Fernández, José J., Hernández Daranas, Antonio
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/226918
Acceso en línea:http://hdl.handle.net/10261/226918
Access Level:acceso abierto
Palabra clave:Free energy
Reaction mechanisms
Chemical structure
Molecular structure
Chemical calculations
Descripción
Sumario:Six novel oxasqualenoids (polyether triterpenes) were isolated from the red alga Laurencia viridis. Laurokanols A–E (1–5) comprise an unreported tricyclic core with a [6,6]-spiroketal system. Yucatecone (6) shows a biogenetically intriguing epimerization at C14. Quantum mechanical calculations were used to corroborate their structures and to explain key steps involved in the biogenetic mechanisms proposed for the formation of oxasqualenoids.