Synthesis 2016; 48(12): 1814-1824
DOI: 10.1055/s-0035-1561589
special topic
© Georg Thieme Verlag Stuttgart · New York

Gold(I)-Catalyzed Enyne Cyclizations: Studies Toward the Total Synthesis of (+)-Aureol

Raphael Wildermuth
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5–13, 81377 München, Germany   eMail: thomas.magauer@lmu.de
,
Klaus Speck
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5–13, 81377 München, Germany   eMail: thomas.magauer@lmu.de
,
Thomas Magauer*
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5–13, 81377 München, Germany   eMail: thomas.magauer@lmu.de
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Publikationsverlauf

Received: 20. Januar 2016

Accepted after revision: 01. März 2016

Publikationsdatum:
12. April 2016 (online)

Abstract

We report a modular synthetic approach toward the total synthesis of (+)-aureol based on a bioinspired gold(I)-catalyzed enyne cascade cyclization reaction. First, we investigated an array of catalysts to promote a 6-endo-dig cyclization of a highly advanced enediyne precursor. Since these studies result exclusively in the formation of the 5-exo-dig product, we synthesized and investigated a dienyne cyclization precursor in order to form the benzo[d]xanthene skeleton in a stepwise fashion.

Supporting Information

 
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