Synthesis of the C1-C9 fragment of the potent antitumor agent dictyostatin

We describe herein a short and efficient synthesis of the C1-C9 fragment of the potent antitumor agent dictyostatin. Notable features of this approach include a Sharpless asymmetric epoxidation followed by epoxide opening under Myashita's conditions to introduce the stereogenic centers at C6 an...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2012-02, Vol.23 (2), p.344-348
Main Authors: Dias, Luiz C., Sant'Ana, Danilo P., Vieira, Ygor W., Gonçalves, Caroline C. S., Lima, Dimas J. P.
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:We describe herein a short and efficient synthesis of the C1-C9 fragment of the potent antitumor agent dictyostatin. Notable features of this approach include a Sharpless asymmetric epoxidation followed by epoxide opening under Myashita's conditions to introduce the stereogenic centers at C6 and C7, and a Horner-Wadsworth-Emmons type reaction under Ando's conditions to construct the Z-double bond of the 1,3-(Z,E)-diene system.
ISSN:0103-5053
1678-4790
DOI:10.1590/S0103-50532012000200022