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. 2009;81(2):195-204.
doi: 10.1351/PAC-CON-08-07-03.

Recent Applications of Imines as Key Intermediates in the Synthesis of Alkaloids and Novel Nitrogen Heterocycles

Stephen F Martin  1
Affiliations

Recent Applications of Imines as Key Intermediates in the Synthesis of Alkaloids and Novel Nitrogen Heterocycles

Stephen F Martin. Pure Appl Chem. 2009.

Abstract

One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (±)-epilupinine (1), (±)-tashiromine (2), (-)-epimyrtine (3), and (±)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

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References

    1. For reviews of N-alkyl iminium ions, see: Blumenkopf TA, Overman LE. Chem Rev. 1986;86:857.Kleinman EF, Volkmann RA. In: Comp Org Syn. Trost BM, editor. 1991. p. 975.Royer J, Bonin M, Micouin L. Chem Rev. 2004;104:2311.For reviews of N-acyl iminium ions, see: Speckamp WN, Moolenaar MJ. Tetrahedron. 2000;56:3817.Maryanoff BE, Zhang HC, Cohen JH, Turchi IJ, Maryanoff CA. Chem Rev. 2004;104:1431.For a review of vinylogous Mannich reactions, see: Martin SF. Acc Chem Res. 2002;35:895.

    1. For selected examples, see: Martin SF, Benage B, Geraci LS, Hunter JE, Mortimore M. J Am Chem Soc. 1991;113:6161.Martin SF, Clark CC, Corbett JW. J Org Chem. 1995;60:3236.Ito M, Clark CC, Mortimore M, Goh JB, Martin SF. J Am Chem Soc. 2001;123:8003.Liras S, Lynch CL, Fryer AM, Vu BT, Martin SF. J Am Chem Soc. 2001;123:5918.Reichelt A, Bur SK, Martin SF. Tetrahedron. 2002;58:6323.Deiters A, Chen K, Eary CT, Martin SF. J Am Chem Soc. 2003;125:4541.Martin SF, Neipp CE. J Org Chem. 2003;68:8867.Washburn DG, Heidebrecht RW, Jr, Martin SF. Org Lett. 2003;5:3523.Rudolph AC, Machauer R, Martin SF. Tetrahedron Lett. 2004;45:4895.Simila STM, Martin SF. J Org Chem. 2007;72:5342.

    1. For a preliminary account of this work, see: Amorde SM, Judd AS, Martin SF. Org Lett. 2005:2031.

    1. For a preliminary account of this work, see: Sunderhaus JD, Dockendorff C, Martin SF. Org Lett. 2007;9:4223. See also references therein for related strategies for rapid assembly of functionalized heterocycles.

    1. Wasserman HH, Vu CB, Cook JD. Tetrahedron. 1992;48:2101.

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