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Synlett 2016; 27(01): 96-100
DOI: 10.1055/s-0035-1560752
letter
© Georg Thieme Verlag Stuttgart · New York

Formal Synthesis of (–)-Siccanin Using an Enantioselective Domino Wacker/Carbonylation/Methoxylation Reaction

Lutz F. Tietze*
Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstraße 2, 37077 Göttingen, Germany   eMail: ltietze@gwdg.de
,
Stefan Jackenkroll
Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstraße 2, 37077 Göttingen, Germany   eMail: ltietze@gwdg.de
,
Dhandapani Ganapathy
Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstraße 2, 37077 Göttingen, Germany   eMail: ltietze@gwdg.de
,
Johannes R. Reiner
Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstraße 2, 37077 Göttingen, Germany   eMail: ltietze@gwdg.de
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Publikationsverlauf

Received: 07. September 2015

Accepted after revision: 01. Oktober 2015

Publikationsdatum:
20. Oktober 2015 (online)

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Dedicated to Professor Steven V. Ley on the occasion of his 70th birthday

Abstract

A formal synthesis of (–)-siccanin was achieved through an enantioselective domino Wacker/carbonylation/methoxylation reaction as the key step to form the chroman ring with a quaternary stereogenic center with 95% ee. The pendant cyclohexyl moiety was introduced through a two-step aldol condensation.

Key words

natural products - domino reaction - aldol reaction - transition-metal catalysis - enantioselective reactions

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560752.
  • Supporting Information
 

  • References and Notes

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