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2004
Alkaloids
U 0600
51- 177
A Concise Formal Synthesis of Alkaloid Cryptotackiene and Substituted 6H-Indolo[2,3-b]quinolines. — Tetracycles (V), precursors for cryptotackiene (VIa) and its
11-methyl derivative (VIb), and aldehyde (VII) are prepared by a short route. It involves the conjugate addition of enolate anions derived from cyclic ketones (II) to
dithioketal (I) as key step. The resulting adducts (III) are cyclized in the presence of
NH4OAc. The methylthio group in compounds (IV) can be either desulfurized (Raney
nickel) or replaced by Me or Ph groups by Ni(II)-catalyzed cross-coupling reactions
with Grignard reagents. — (SUNDARAM, G. S. M.; VENKATESH, C.; KUMAR, U.
K. S.; ILA*, H.; JUNJAPPA, H.; J. Org. Chem. 69 (2004) 17, 5760-5762; Dep.
Chem., Indian Inst. Technol., Kanpur 208 016, India; Eng.) — Klein
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