Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (-)-Epiglobulol and (-)-4β,7α- and (-)-4α,7α-Aromadendranediols

Identificador:  imarina:9440806

Handle: https://hdl.handle.net/20.500.11797/imarina9440806

Autors:  Carreras, Javier; Livendahl, Madeleine; McGonigal, Paul R; Echavarren, Antonio M

Resum:
Three natural aromadendrane sesquiterpenes, (-)-epiglobulol, (-)-4,7-aromadendranediol, and (-)-4,7-aromadendranediol, have been synthesized in only seven steps in 12, 15, and 17% overall yields, respectively, from (E,E)-farnesol by a stereodivergent gold(I)-catalyzed cascade reaction which forms the tricyclic aromadendrane core in a single step. These are the shortest total syntheses of these natural compounds.