A convergent and enantioselective synthesis of (+)-amurensinine via selective C-H and C-C bond insertion reactions

doi:10.1021/ja0651815

. 2006 Sep 13;128(36):11752-3.

doi: 10.1021/ja0651815.

A convergent and enantioselective synthesis of (+)-amurensinine via selective C-H and C-C bond insertion reactions

Uttam K Tambar¹, David C Ebner, Brian M Stoltz

Affiliations

PMID: 16953603
PMCID: PMC2529249
DOI: 10.1021/ja0651815

A convergent and enantioselective synthesis of (+)-amurensinine via selective C-H and C-C bond insertion reactions

Uttam K Tambar et al. J Am Chem Soc. 2006.

. 2006 Sep 13;128(36):11752-3.

doi: 10.1021/ja0651815.

Authors

Uttam K Tambar¹, David C Ebner, Brian M Stoltz

Affiliation

¹ Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

PMID: 16953603
PMCID: PMC2529249
DOI: 10.1021/ja0651815

Abstract

A convergent and enantioselective synthesis of the natural product amurensinine is described. The synthetic strategy takes advantage of mild and selective C-H and C-C bond insertion reactions, in addition to the palladium-catalyzed aerobic oxidative kinetic resolution recently developed in these laboratories.

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**Figure 1**
Representative isopavine natural products.

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References

1. Kakiuchi F, Murai S. Topics in Organometallic Chemistry Series. In: Murai S, editor. Activation of Unreactive Bonds and Organic Synthesis. Vol. 3. Springer-Verlag; Berlin and New York: 1999. pp. 47–79.
2. Murakami M, Ito Y. Topics in Organometallic Chemistry Series. In: Murai S, editor. Activation of Unreactive Bonds and Organic Synthesis. Vol. 3. Springer-Verlag; Berlin and New York: 1999. pp. 97–129.
3. Crabtree RH. Chem. Rev. 1985;85:245–269.
4. Labinger JA, Bercaw JE. Nature. 2002;417:507–514. - PubMed
5. Davies HML, Beckwith REJ. Chem. Rev. 2003;103:2861–2903. - PubMed
1. For recent examples, see: Davies HML, Dai X, Long MS. J. Am. Chem. Soc. 2006;128:2485–2490.O'Malley SJ, Tan KL, Watzke A, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2005;127:13496–13497.Kurosawa W, Kobayashi H, Kan T, Fukuyama T. Tetrahedron. 2004;60:9615–9628.Wehn PM, Du Bois J. J. Am. Chem. Soc. 2002;124:12950–12951.Johnson JA, Li N, Sames D. J. Am. Chem. Soc. 2002;124:6900–6903.
1. Boit HG, Flentje H. Naturwiss. 1960;47:180.
2. Gözler B, Lantz MS, Shamma M. J. Nat. Prod. 1983;46:293–309.
1. For selected syntheses of isopavine alkaloids, see: Gözler B. Pavine and Isopavine Alkaloids. In: Brossi A, editor. The Alkaloids. Vol. 31. Academic Press; New York: 1987. pp. 343–356.Shinohara T, Takeda A, Toda J, Sano T. Heterocycles. 1998;48:981–992.Gottlieb L, Meyers AIJ. Org. Chem. 1990;55:5659–5662.Hanessian S, Mauduit M. Angew. Chem., Int. Ed. 2001;40:3810–3813.Dragoli DR, Burdett MT, Ellman JA. J. Am. Chem. Soc. 2001;123:10127–10128.
1. For discussions on the biological activity of the isopavine alkaloids, see: Weber E, Keana J, Barmettler P. PCT Int. Appl. WO 12575, 1990. Chem. Abstr. 1991;115:106019w.Childers WE, Abou-Gharbia MA. Chem. Abstr. U.S. Patent 4940789, 1990 1990. p. 191190w.

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[1] Kakiuchi F, Murai S. Topics in Organometallic Chemistry Series. In: Murai S, editor. Activation of Unreactive Bonds and Organic Synthesis. Vol. 3. Springer-Verlag; Berlin and New York: 1999. pp. 47–79.

Murakami M, Ito Y. Topics in Organometallic Chemistry Series. In: Murai S, editor. Activation of Unreactive Bonds and Organic Synthesis. Vol. 3. Springer-Verlag; Berlin and New York: 1999. pp. 97–129.

Crabtree RH. Chem. Rev. 1985;85:245–269.

Labinger JA, Bercaw JE. Nature. 2002;417:507–514. - PubMed

Davies HML, Beckwith REJ. Chem. Rev. 2003;103:2861–2903. - PubMed

[2] Kakiuchi F, Murai S. Topics in Organometallic Chemistry Series. In: Murai S, editor. Activation of Unreactive Bonds and Organic Synthesis. Vol. 3. Springer-Verlag; Berlin and New York: 1999. pp. 47–79.

[3] Murakami M, Ito Y. Topics in Organometallic Chemistry Series. In: Murai S, editor. Activation of Unreactive Bonds and Organic Synthesis. Vol. 3. Springer-Verlag; Berlin and New York: 1999. pp. 97–129.

[4] Crabtree RH. Chem. Rev. 1985;85:245–269.

[5] Labinger JA, Bercaw JE. Nature. 2002;417:507–514. - PubMed

[6] Davies HML, Beckwith REJ. Chem. Rev. 2003;103:2861–2903. - PubMed

[7] For recent examples, see: Davies HML, Dai X, Long MS. J. Am. Chem. Soc. 2006;128:2485–2490.O'Malley SJ, Tan KL, Watzke A, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2005;127:13496–13497.Kurosawa W, Kobayashi H, Kan T, Fukuyama T. Tetrahedron. 2004;60:9615–9628.Wehn PM, Du Bois J. J. Am. Chem. Soc. 2002;124:12950–12951.Johnson JA, Li N, Sames D. J. Am. Chem. Soc. 2002;124:6900–6903.

[8] For recent examples, see: Davies HML, Dai X, Long MS. J. Am. Chem. Soc. 2006;128:2485–2490.O'Malley SJ, Tan KL, Watzke A, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2005;127:13496–13497.Kurosawa W, Kobayashi H, Kan T, Fukuyama T. Tetrahedron. 2004;60:9615–9628.Wehn PM, Du Bois J. J. Am. Chem. Soc. 2002;124:12950–12951.Johnson JA, Li N, Sames D. J. Am. Chem. Soc. 2002;124:6900–6903.

[9] Boit HG, Flentje H. Naturwiss. 1960;47:180.

Gözler B, Lantz MS, Shamma M. J. Nat. Prod. 1983;46:293–309.

[10] Boit HG, Flentje H. Naturwiss. 1960;47:180.

[11] Gözler B, Lantz MS, Shamma M. J. Nat. Prod. 1983;46:293–309.

[12] For selected syntheses of isopavine alkaloids, see: Gözler B. Pavine and Isopavine Alkaloids. In: Brossi A, editor. The Alkaloids. Vol. 31. Academic Press; New York: 1987. pp. 343–356.Shinohara T, Takeda A, Toda J, Sano T. Heterocycles. 1998;48:981–992.Gottlieb L, Meyers AIJ. Org. Chem. 1990;55:5659–5662.Hanessian S, Mauduit M. Angew. Chem., Int. Ed. 2001;40:3810–3813.Dragoli DR, Burdett MT, Ellman JA. J. Am. Chem. Soc. 2001;123:10127–10128.

[13] For selected syntheses of isopavine alkaloids, see: Gözler B. Pavine and Isopavine Alkaloids. In: Brossi A, editor. The Alkaloids. Vol. 31. Academic Press; New York: 1987. pp. 343–356.Shinohara T, Takeda A, Toda J, Sano T. Heterocycles. 1998;48:981–992.Gottlieb L, Meyers AIJ. Org. Chem. 1990;55:5659–5662.Hanessian S, Mauduit M. Angew. Chem., Int. Ed. 2001;40:3810–3813.Dragoli DR, Burdett MT, Ellman JA. J. Am. Chem. Soc. 2001;123:10127–10128.

[14] For discussions on the biological activity of the isopavine alkaloids, see: Weber E, Keana J, Barmettler P. PCT Int. Appl. WO 12575, 1990. Chem. Abstr. 1991;115:106019w.Childers WE, Abou-Gharbia MA. Chem. Abstr. U.S. Patent 4940789, 1990 1990. p. 191190w.

[15] For discussions on the biological activity of the isopavine alkaloids, see: Weber E, Keana J, Barmettler P. PCT Int. Appl. WO 12575, 1990. Chem. Abstr. 1991;115:106019w.Childers WE, Abou-Gharbia MA. Chem. Abstr. U.S. Patent 4940789, 1990 1990. p. 191190w.

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A convergent and enantioselective synthesis of (+)-amurensinine via selective C-H and C-C bond insertion reactions

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A convergent and enantioselective synthesis of (+)-amurensinine via selective C-H and C-C bond insertion reactions

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Abstract

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Abstract

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