Abstract
We have discovered that several platinum- or gold-catalyzed cycloisomerization
reactions can also be catalyzed by copper. This Account discusses
our new findings, the complementarity of copper-catalysis, and its
application to the synthesis of (-)-cubebol, (-)-β-santalol,
and other fragrance compounds.
1 Introduction
2 Cycloisomerization of 5-en-1-yn-3-ols: The Cyclopropanation
Pathway
3 Cycloisomerization of 5-En-1-yn-3-ol-Derived Esters and Synthesis
of (-)-Cubebol
4 Cycloisomerization of a 6-En-1-yn-3-ol and Its Corresponding
Acetate towards the Synthesis of Thujopsanone-Like Compounds
5 Cyclization-Fragmentations of 5-En-1-yn-3-ols
6 Synthesis of (-)-β-Santalol by Cyclization-Fragmentation of
a 5-En-1-yn-3-ol
7 Reactivity of 6-En-1-yn-4-ols: Cyclization-Fragmentation vs.
Metathesis Reaction
8 Conclusions and Outlook
Key words
copper catalysis - cycloisomerizations - fragrances - alkynes - gold catalysis
References and Notes
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