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Synthesis 2012(7): 1051-1056  
DOI: 10.1055/s-0031-1289745
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of the AB-DE Ring System Present in the Alstoscholarine Alkaloids

Luis A. Polindara-García, Luis D. Miranda*
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior S.N., Ciudad Universitaria, Coyoacán, México, D.F. 04510, México
Fax: +52(55)56162217; e-Mail: lmiranda@unam.mx;
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Publikationsverlauf

Received 3 January 2012
Publikationsdatum:
15. März 2012 (online)

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Abstract

A practical protocol is presented for the construction of the AB-DE rings present in (19,20)-(E)- and (19,20)-(Z)-alstoscholarine alkaloids from the commercially available glutamic acid 5-methyl ester, employing only a six-step synthetic sequence. The main features include the synthesis of the alkynylindolizinone core and the use of Sonogashira cross-coupling and base-mediated cyclization to afford a 2-substituted indole without the use of protecting groups.

Key words

alkaloids - indoles - pyrroles - cross-coupling - heterocycles

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CCDC 856985 (3) contains the supplementary crystallographic data for this paper. Copies of these data can be obtained, free of charge, from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.