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2005
Alkaloids
U 0600
06- 184
Application of a Catalytic Palladium Biaryl Synthesis Reaction, via C—H Functionalization, to the Total Synthesis of Amaryllidaceae Alkaloids. — The palladium-catalyzed cyclization of indole derivatives (I) affords fused phenanthridine compounds (II) which are hydrolyzed to give the corresponding diones (III). Reduction of
these diones employing BH3·THF gives single product (IV) in the case of derivative
(IIIa), but unseparable mixtures of two reduction products analogous to compounds
(IV) and (V) in the case of diones (IIIb) and (IIIc). As a consequence, target alkaloids
anhydrolycorin-7-one (VIb), oxoassoanine (VIc), hippadine (VIIb) and pratosine
(VIIc) are obtained starting from diones (III) by a reduction/reduction/oxidation
sequence and a reduction/oxidation sequence correspondingly, without purification of
the intermediates. — (TORRES, J. C.; PINTO, A. C.; GARDEN*, S. J.; Tetrahedron
60 (2004) 44, 9889-9900; Dep. Quim. Org., Inst. Quim., Univ. Fed. Rio de Janeiro,
21945 Rio de Janeiro, Brazil; Eng.) — Klein
2005
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