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Synthesis 2015; 47(13): 1922-1936
DOI: 10.1055/s-0034-1380192
paper
© Georg Thieme Verlag Stuttgart · New York

Toward a Synthetic Access to Jatropha-5,12-dienes by Ring-Closing Metathesis: Detours and Dead-Ends

Lena Butt
Fakultät Chemie und Chemische Biologie, Technische Universität Dortmund, 44227 Dortmund, Germany   eMail: martin.hiersemann@tu-dortmund.de
,
Christoph Schnabel
Fakultät Chemie und Chemische Biologie, Technische Universität Dortmund, 44227 Dortmund, Germany   eMail: martin.hiersemann@tu-dortmund.de
,
Martin Hiersemann*
Fakultät Chemie und Chemische Biologie, Technische Universität Dortmund, 44227 Dortmund, Germany   eMail: martin.hiersemann@tu-dortmund.de
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Publikationsverlauf

Received: 23. Januar 2015

Accepted: 09. März 2015

Publikationsdatum:
13. April 2015 (online)

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Abstract

Results from efforts aimed at the synthesis of polyhydroxylated jatropha-5,12-dienes are unveiled. An apparently pre-qualified plot consisting of successive aldol addition and ring-closing metathesis was pursued in order to construct the fully oxidized trans-bicy­clo[10.3.0]pentadecane scaffold of naturally occurring jatrophanoids.

Key words

terpenoids - total synthesis - aldol reaction - ring closure - metathesis

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380192.
  • Supporting Information
 

  • References


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