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Synlett 2011(1): 6-29
DOI: 10.1055/s-0030-1259104
DOI: 10.1055/s-0030-1259104
ACCOUNT
© Georg Thieme Verlag
Stuttgart ˙ New YorkPalladium-Catalyzed Synthesis of N- and O-Heterocycles Starting from Enol Phosphates
Further Information
Received
24 August 2010
Publication Date:
10 December 2010 (online)
Publication History
Publication Date:
10 December 2010 (online)
Abstract
In this Account, we describe our efforts in the development of new synthetic strategies for the construction of N- and O-heterocycles by exploiting palladium-catalyzed reactions using enol phosphates as an electrophilic component.
1 Introduction
2 Suzuki-Miyaura Coupling of Lactone-Derived Enol Phosphates: A Convergent Synthetic Strategy toward trans-Fused Polycyclic Ether Marine Metabolites
3 Domino Intramolecular Heck/Diels-Alder Reaction of Imide-Derived Enol Phosphates toward the Synthesis of Fused N-Heterocycles
4 Strategies for the Synthesis of 2-Substituted Indoles and Indolines via Suzuki-Miyaura Coupling of Imide-Derived Enol Phosphates
5 Palladium-Catalyzed Reduction of Enol Phosphates: Total Synthesis of (±)-Lennoxamine and (±)-Chilenine
6 Suzuki-Miyaura Coupling of an Acetate-Derived Enol Phosphate: Total Synthesis of (+)-Neopeltolide
7 Concluding Remarks
Key words
palladium - cross-coupling - phosphates - heterocycles - fused-ring systems - natural products
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References
Orito et al. have independently reported the same strategy for the synthesis of (±)-lennoxamine and (±)-chilenine from enamide 135. See ref. 88a.