Synthesis of hexahydrocarbazoles by cyclisation of 3-(but-3-enyl) indole derivatives

A new cyclisation of 3-(but-3-enyl) indole derivatives that produces policyclic compounds with a hexahydrocarbazole structure is described. In this reaction three stereogenic centres are generated in one step, and this process can be considered as evidence of the biogenetic relationship between anom...

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Bibliographic Details
Published in:Tetrahedron 2009-12, Vol.65 (49), p.10235-10242
Main Authors: Marcos, Isidro S., Moro, Rosalina F., Costales, Isabel, Escola, Miguel A., Basabe, Pilar, Díez, David, Urones, Julio G.
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Anominine
Chemistry
Condensed benzenic and aromatic compounds
ent-Halimic acid
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indol diterpenes
Organic chemistry
Preparations and properties
Terpenoids
Thiersindole
Tubingensin A
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Summary:A new cyclisation of 3-(but-3-enyl) indole derivatives that produces policyclic compounds with a hexahydrocarbazole structure is described. In this reaction three stereogenic centres are generated in one step, and this process can be considered as evidence of the biogenetic relationship between anominine and tubingensin A. A new cyclisation of 3-(but-3-enyl) indole derivatives to give hexahydrocarbazole structure, generating three stereogenic centres in one step, is described. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.09.090