Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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
See this image and copyright information in PMC

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

Publication types