A number of isoquinoline alkaloids with significant bioactivity have the stereocenter located at the quaternary carbon atom in the a-nitrogen position.[1] The Erythrina family e.g. erytramine contain pyrrolo-isoquinoline skeleton, while tetrahydroisoquinoline motif is present in a variety of natural products including cactus alkaloids (Pevoruvic acid), mammalian alkaloids (Salsoline-1-carboxylic acid), Ecteinascidine family (ET 743), and spirobenzoquinoline alkaloids (Parfumine, Figure 1).

  Figure 1.

 The stereoselective synthesis of isoquinoline alkaloids with quaternary carbon stereocenter is not trivial, and generally utilize a chiral starting material. We have recently described a simple stereocontrolled synthesis of 10b-substituted hexahydropyrrolo-isoquinolines 1 from L-tartaric acid [2, 3]. The easy transformation of 1 into optically salsolinol and salsoline-1-carboxylic acid will be reported. (Scheme 1) The new strategy for the synthesis of Erythrina family alkaloids will be discussed. 

Scheme 1

References:

[1]. Bentley, K. W. The Isoquinoline Alkaloids; Harwood Academic, Amsterdam, 1998.

[2]. Mostowicz, D.; Wójcik, R.; Dołęga, G.; Kałuża, Z. Tetrahedron Letters, 45, 6011-6015, 2004.

[3]. Kałuża, Z.; Mostowicz, D.; Dołęga, G.; Mroczko,  K.; Wójcik R. Tetrahedron 62, 943-953, 2006.

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