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Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)‐Epiglobulol and (−)‐4β,7α‐ and (−)‐4α,7α‐Aromadendranediols
Author(s) -
Carreras Javier,
Livendahl Madeleine,
McGonigal Paul R.,
Echavarren Antonio M.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201402044
Subject(s) - farnesol , cascade , stereochemistry , chemistry , core (optical fiber) , tricyclic , combinatorial chemistry , organic chemistry , computer science , chromatography , telecommunications
Three natural aromadendrane sesquiterpenes, (−)‐epiglobulol, (−)‐4β,7α‐aromadendranediol, and (−)‐4α,7α‐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.