Issue 21, 2004
From the journal:

Organic & Biomolecular Chemistry

Spirobicyclo[2.2.2]octane derivatives: mimetics of baccatin III and paclitaxel (Taxol)†‡

Fredrik Almqvist,a   Sophie Manner,b   Viveca Thornqvist,b   Ulf Berg,b   Margareta Wallinc  and  Torbjörn Frejd*b  

* Corresponding authors

a Department of Organic Chemistry, Umeå University, Umeå, Sweden

b The Laboratory of Organic and Bioorganic Chemistry, Department of Chemistry, Lund University, P. O. Box 124, Lund, Sweden
E-mail: Torbjorn.Frejd@orgk1.lu.se

c Department of Zoology, Göteborg University, P.O. Box 463, Göteborg, Sweden

Abstract

The formylated spirobyclic alcohol 8a was computer modeled to be a mimetic of paclitaxel. In this model, the formyl group was used as a truncated paclitaxel side chain in order to reduce the computational work. Compound 8c, carrying the paclitaxel side chain, was synthesized in six steps from optically active 1,3-diketone 12. Microtubule stabilization was not observed for 8c, indicating that the model needs to be adjusted.

Graphical abstract: Spirobicyclo[2.2.2]octane derivatives: mimetics of baccatin III and paclitaxel (Taxol)

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Article information

DOI
https://doi.org/10.1039/B409678A
Article type
Paper
Submitted
25 Jun 2004
Accepted
03 Sep 2004
First published
04 Oct 2004

Org. Biomol. Chem., 2004,2, 3085-3090

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Spirobicyclo[2.2.2]octane derivatives: mimetics of baccatin III and paclitaxel (Taxol)

F. Almqvist, S. Manner, V. Thornqvist, U. Berg, M. Wallin and T. Frejd, Org. Biomol. Chem., 2004, 2, 3085 DOI: 10.1039/B409678A

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