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Org Lett. 2005 May 12;7(10):2019-22.

A desymmetrization route to fused Troger's base analogues: synthesis, isolation, and characterization of the first anti-anti diastereomer of a fused tris-Troger's base analogue.

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  • 1Organic Chemistry, Department of Chemistry, Lund University, Sweden.

Abstract

A desymmetrization route to fused Troger's base analogues was developed. In this way, the synthesis of the first example of an anti-anti diastereomer of a fused tris-Troger's base analogue was accomplished. The resulting compound 5b is a nonlinear symmetric regioisomer obtained from p-bromoaniline in 7% yield. The corresponding syn-anti diastereomer 5a was obtained in 4% yield.

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