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2004
Alkaloids
U 0600
49- 188
Enantioselective Formal Synthesis of Uleine Alkaloids from Phenylglycinol-Derived Bicyclic Lactams. — A two-step route for the construction of the tetracyclic ring
system of uleine alkaloids is described. The approach involves the stereoselective conjugate addition of an appropriate indole-containing nucleophile to a chiral bicyclic
δ-lactam and the subsequent cyclization on the indole 3-position of the resulting 4,5-disubstituted 2-piperidone. The sequence is used in the formal synthesis of several alkaloids of this group. — (AMAT*, M.; PEREZ, M.; LLOR, N.; MARTINELLI, M.;
MOLINS, E.; BOSCH*, J.; Chem. Commun. (Cambridge) 2004, 14, 1602-1603;
Lab. Quim. Org., Fac. Farm., Univ. Barcelona, E-08028 Barcelona, Spain; Eng.) —
M. Paetzel
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