Polycyclic framework synthesis of anominine and tubingensin A indole diterpenoids

Ben Bradshaw; Gorka Etxebarria-Jardí; Josep Bonjoch

doi:10.1039/B718280E

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Polycyclic framework synthesis of anominine and tubingensin Aindole diterpenoids†

Ben Bradshaw,^a Gorka Etxebarria-Jardí^a and Josep Bonjoch*^a

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* Corresponding authors

^a Laboratori de Química Orgànica, Facultat de Farmàcia, Institut de Biomedicina (IBUB), Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain
E-mail: josep.bonjoch@ub.edu
Fax: +34 934024539

Abstract

A highly congested decalin embodying an α-methylene ketone is synthesized in 11 steps from the Wieland–Miescher ketone and efficiently converted to the polycyclic frameworks of anominine and tubingensin A, which constitutes the first approach to the skeleton of these indole diterpenoids.

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Supplementary files

¹³C NMR chemical shifts of all compounds (Table 1) and copies of selected ¹H and ¹³C NMR spectra PDF (2722K)

Article information

DOI: https://doi.org/10.1039/B718280E
Article type: Paper
Submitted: 27 Nov 2007
Accepted: 18 Dec 2007
First published: 17 Jan 2008

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Org. Biomol. Chem., 2008,6, 772-778

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Polycyclic framework synthesis of anominine and tubingensin A indole diterpenoids

B. Bradshaw, G. Etxebarria-Jardí and J. Bonjoch, Org. Biomol. Chem., 2008, 6, 772 DOI: 10.1039/B718280E

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Organic & Biomolecular Chemistry

Polycyclic framework synthesis of anominine and tubingensin Aindole diterpenoids†

Abstract

Supplementary files

Article information

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Polycyclic framework synthesis of anominine and tubingensin A indole diterpenoids

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