Preparation of Annulated Nitrogen Containing Heterocycles via a One-Pot Palladium-Catalyzed Alkylation/Direct Arylation Sequence Christophe Blaszykowski, Evangelos Aktoudianakis, Cyril Bressy, Dino Alberico and Mark Lautens, Org. Lett. ASAP University of Toronto Dhanalakshmi Kasi 6 May 2006 Dhana Kasi @ Wipf Group 1 5/10/2006
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Preparation of Annulated Nitrogen ContainingHeterocycles via a One-Pot Palladium-Catalyzed
Alkylation/Direct Arylation Sequence
Christophe Blaszykowski, Evangelos Aktoudianakis, Cyril Bressy, DinoAlberico and Mark Lautens, Org. Lett. ASAP
University of Toronto
Dhanalakshmi Kasi
6 May 2006
Dhana Kasi @ Wipf Group 1 5/10/2006
Natural Products Containing Tricyclic Structure 1
Crispine A: Isolated from Carduus crispus –cyctotoxic activity
Lettowianthin: Isolated from Lettowianthus stellatus
Lammelarin D: Marine Alkaloid, potent cytotoxic.
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Annulation of Indole via Indole Radicals: Addition ofthe 2-Indolyl Radical to Aromatic Rings
N
Br
CHO
MeCN
N
CHO
N
CHO
( )n
Bu3SnH, AIBN
( )n
( )n
+
n = 1 55% 25%
n = 2 20% 65%
n = 3 32% 37%
Fiumana, A.; Jones, K. Tet. Lett. 2000, 41, 4209-4211
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Synthetic Applications of Aryl radical Building Blocksfor Cyclization onto Azoles