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2005
Alkaloids
U 0600
30- 183
A New Asymmetric Synthesis of 2,6-cis-Disubstituted 4-Methylenepiperidines:
Total Synthesis of (+)-Alkaloid 241D and (+)-Isosolenopsin A. — Title compounds
are formed with good yields, excellent diastereoselectivity and good enantioselectivity
by a Mannich-type reaction of disilanes (I) or (VI) with aldehydes or ketones. A similar
reaction of allylsilane (X) also affords these piperidines but only with moderate enantioselectivities. Alkaloid 241D (IV) and isosolenopsin A (V) can be readily prepared
by further elaboration of piperidines (Ia) and (Ib). — (MONFRAY, J.;
GELAS-MIALHE, Y.; GRAMAIN, J.-C.; REMUSON*, R.; Tetrahedron: Asymmetry
16 (2005) 5, 1025-1034; CNRS, Univ. Blaise Pascal, F-63177 Aubiere, Fr.; Eng.) —
Klein
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