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. 2013 Sep 6;15(17):4580-3.
doi: 10.1021/ol402188b. Epub 2013 Aug 20.

Access to the protoilludane core by gold-catalyzed allene-vinylcyclopropane cycloisomerization

Anthony Pitaval  1 , David Leboeuf, Julien Ceccon, Antonio M Echavarren
Affiliations

Access to the protoilludane core by gold-catalyzed allene-vinylcyclopropane cycloisomerization

Anthony Pitaval et al. Org Lett. .

Erratum in

  • Org Lett. 2013 Oct 4;15(19):5146

Abstract

Gold(I)-catalyzed allene-vinylcyclopropane cycloisomerization leads to the tricyclic framework of the protoilludanes in a single step by a reaction that involves a cyclopropane ring expansion and a Prins cyclization.

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Figures

Figure 1
Figure 1
Representative protoilludane sesquiterpenes.
Scheme 1
Scheme 1. Gold(I)-Catalyzed Cycloisomerization of Cyclopropylenyne 5(11)
Scheme 2
Scheme 2. Gold-Catalyzed Allene-vinylcyclopropane Cycloisomerization
Scheme 3
Scheme 3. Gold(I)-Catalyzed Cyclization of Allene-E-vinylcyclopropanes E-7 and 9
Scheme 4
Scheme 4. Synthesis of Substrate Z-7
Scheme 5
Scheme 5. Gold(I)-Catalyzed Cyclization of Z-7
Figure 2
Figure 2
X-ray structures of 19 (a) and 20 (b).
Scheme 6
Scheme 6. Transformations of Compounds 18a and 18b
Scheme 7
Scheme 7. Stereospecific Cyclizations of E- and Z-I
See this image and copyright information in PMC

References

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