Title: A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation.
Authors: Rosales Martínez, Antonio; Enríquez, Lourdes; Jaraíz, Martín; Pozo Morales, Laura; Rodríguez-García, Ignacio; Díaz Ojeda, Emilio
Abstract: 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.
Subjects: NATURAL products
Publication: Marine Drugs, 2020, Vol 18, Issue 9, p441
ISSN: 1660-3397
Publication type: Academic Journal
DOI: 10.3390/md18090441

A Concise Route for the Synthesis of Tetracyclic Meroterpenoids: (±)-Aureol Preparation and Mechanistic Interpretation.

Rosales Martínez, Antonio; Enríquez, Lourdes; Jaraíz, Martín; Pozo Morales, Laura; Rodríguez-García, Ignacio; Díaz Ojeda, Emilio