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Synlett 2013; 24(8): 955-958
DOI: 10.1055/s-0032-1316899
letter
© Georg Thieme Verlag Stuttgart · New York

Approach to the Core Structure of the Polycyclic Alkaloid Palhinine A

Dominik Gaugele
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany   Fax: +49(7071)295137   Email: martin.e.maier@uni-tuebingen.de
,
Martin E. Maier*
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany   Fax: +49(7071)295137   Email: martin.e.maier@uni-tuebingen.de
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Publication History

Received: 11 February 2013

Accepted after revision: 18 March 2013

Publication Date:
09 April 2013 (online)

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Abstract

A synthesis of the tricyclic partly substituted core structure of palhinine A was achieved. To reach the bicyclo[2.2.2]octane motif a domino Michael reaction was employed as a key step. After Arndt–Eistert homologation and intramolecular aldol reaction the isotwistane core could be obtained after simple functional-group manipulations.

Key words

palhinine A - domino Michael reaction - X-ray crystal structure - Arndt–Eistert homologation - intramolecular aldol re­action

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information

Primary Data

    for this article are available online at ­http://www.thieme-connect.com/ejournals/toc/synlett and can be cited using the following DOI: 10.4125/pd0043th.
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  • References and Notes

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