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. 2011:7:1007-13.
doi: 10.3762/bjoc.7.114. Epub 2011 Jul 22.

One-pot Diels-Alder cycloaddition/gold(I)-catalyzed 6-endo-dig cyclization for the synthesis of the complex bicyclo[3.3.1]alkenone framework

Boubacar Sow  1 , Gabriel Bellavance, Francis Barabé, Louis Barriault
Affiliations

One-pot Diels-Alder cycloaddition/gold(I)-catalyzed 6-endo-dig cyclization for the synthesis of the complex bicyclo[3.3.1]alkenone framework

Boubacar Sow et al. Beilstein J Org Chem. 2011.

Abstract

The rapid synthesis of bicyclo[m.n.1]alkanone cores possessing quaternary carbon centers adjacent to a bridged ketone represents a significant synthetic challenge. This type of architectural feature is embedded in various complex biologically active compounds such as hyperforin and garsubellin A. Herein, we report a highly diastereoselective one-pot Diels-Alder reaction/Au(I)-catalyzed carbocyclization to generate bicyclo[3.3.1]alkanones in yields ranging from 48-93%.

Keywords: Diels–Alder; bicyclo[3.3.1]nonenone; carbocyclization; gold catalysis; one-pot process.

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Figures

Figure 1
Figure 1
Structures of naturally occurring PPAPs.
Scheme 1
Scheme 1
Gold(I)-catalyzed 6-endo-dig cyclization.
Scheme 2
Scheme 2
Synthesis of papuaforin A core 4.
Scheme 3
Scheme 3
Proposed domino Diels–Alder reaction/gold(I)-catalyzed cyclization.
Scheme 4
Scheme 4
One-pot Diels–Alder cycloaddition/gold(I) catalyzed carbocyclization.
See this image and copyright information in PMC

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