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2004
Alkaloids
U 0600
48- 176
Unprecedented Stereospecific Synthesis of a Novel Tetracyclic Ring System,
a Hybrid of Tetrahydropyrrolo[2,3-b]indole and Tetrahydroimidazo[1,2-a]indole,
via a Domino Reaction upon a Tryptophan-Derived Amino Nitrile. —
The acid-mediated stereospecific domino tautomerization of nitrile (I) gives access
to novel tetracyclic amidine and lactam derivatives. Under the optimized conditions
shown, (II) is obtained as a single product. Varying the concentration of the acid in
CH2Cl 2 leads to additional formation of (III)-(V). — (GONZALEZ-VERA, J. A.;
GARCIA-LOPEZ, M. T.; HERRANZ*, R.; Org. Lett. 6 (2004) 16, 2641-2644; Inst.
Quim. Med., CSIC, E-28006 Madrid, Spain; Eng.) — Steudel
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