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. 2007 Jan 4;9(1):5-8.
doi: 10.1021/ol062017d.

Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis

Gustavo Moura-Letts  1 , Dennis P Curran
Affiliations

Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis

Gustavo Moura-Letts et al. Org Lett. .

Abstract

[reaction: see text] Cross metathesis of terminal alkenes with methyl (2Z,4E)-hexadienoate and related dienyl esters provides substituted (2Z,4E)-dienyl esters in good yields. Small-scale reactions are effectively promoted by the standard second-generation Grubbs-Hoveyda catalyst (GH-II), while a new fluorous GH-II catalyst is used for separation and recovery in gram-scale reactions. The transformation is featured in a rapid synthesis of the bottom fragments of the potent anticancer agents (-)-dictyostatin and 6-epi-dictyostatin.

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Figures

Figure 1
Figure 1
Structure of dictyostatin 1 and ene-diene cross metathesis approach to the (2E,4E)-dienyl ester fragment.
Figure 2
Figure 2
Structures of metathesis catalysts
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References

    1. Pettit GR, Cichacz ZA, Gao F, Boyd MR, Schmidt JM. J Chem Soc, Chem Commun. 1994:1111–1112.
    2. Isbrucker RA, Cummins J, Pomponi SA, Longley RE, Wright AE. Biochem Pharm. 2003;66:75–82. - PubMed
    3. Paterson I, Britton R, Delgado O, Wright AE. Chem Commun. 2004:632–633. - PubMed
    1. Paterson I, Anderson EA. Science. 2005;310:451–453. - PubMed
    2. Gunasekera SP, Wright AE. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, editors. CRC Taylor Francis; New York, NY: 2005. pp. 171–189.
    1. Shin Y, Choy N, Turner TR, Balachandran R, Madiraju C, Day BW, Curran DP. Org Lett. 2002;4:4443–4446. - PubMed
    2. Paterson I, Britton R, Delgado O, Meyer A, Poullennec KG. Angew Chem Int Ed. 2004;43:4629–4633. - PubMed
    3. Shin Y, Fournier JH, Fukui Y, Bruckner AM, Curran DP. Angew Chem Int Ed. 2004;43:4634–4637. - PubMed
    4. Shin Y, Fournier JH, Balachandran R, Madiraju C, Raccor BS, Zhu G, Edler MC, Hamel E, Day BW, Curran DP. Org Lett. 2005;7:2873–2876. - PubMed
    5. O’Neil GW, Phillips AJ. J Am Chem Soc. 2006;128:5340–5341. - PubMed
    6. Fukui Y, Brückner AM, Shin Y, Balachandran R, Day BW, Curran DP. Org Lett. 2006;8:301–304. - PubMed
    7. Jagel J, Maier ME. Synlett. 2006:693–696.
    8. Shin Y, Fournier J-H, Brückner A, Madiraju C, Edler MC, Vogt A, Balachandran R, Raccor BS, Zhu G, Hamel E, Day BW, Curran DP. manuscript in preparation.
    9. Jung W-H, Harrison C-H, Shin Y, Fournier J-H, Madiraju C, Edler MC, Vogt A, Balachandran R, Raccor BS, Zhu G, Hamel E, Day BW, Curran DP. manuscript in preparation.
    1. Grubbs RH, Trnka TM. In: Ruthenium in Organic Synthesis. Murahashi S-I, editor. Wiley-VCH; Weinheim: 2004. pp. 153–178.
    2. Grubbs RH. Handbook of Metathesis. Wiley-VCH; Weinheim: 2003.
    3. Fürstner A. Angew Chem Int Ed. 2000;39:3012–3043. - PubMed
    4. Schuster M, Blechert S. Angew Chem Int Ed Engl. 1997:2037–2056.
    5. Diver ST, Giessert AJ. Chem Rev. 2004;104:1317–1382. - PubMed
    1. Funk TW, Efskind J, Grubbs RH. Org Lett. 2005;7:187–190. - PubMed

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