b-Ketoesters Derived from Pyroglutamic Acid: New Entry to Hydroxylated Pyrrolizidinones

Fused pyrrole derivatives R 0160 β-Ketoesters Derived from Pyroglutamic Acid: New Entry to Hydroxylated Pyrrolizidinones. -The stereoselective catalytic hydrogenation of β-hydroxyesters (I) and (VII) is applied for the preparation of hydroxylated pyrrolizidinones (VI) and (XII). The use of RuBr2((S)-BINAP) allows to prepare the corresponding 7-epimers of compounds (VI) and (XII). -(LE BOUC, G.; THOMASSIGNY, C.; GRECK*, C.; Heterocycles 75 (2008) 10, 2541-2547; Inst. Lavoisier, CNRS, Univ. Versailles St. Quentin, F-78035 Versailles, Fr.; Eng.) -R. Staver 07-130

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ChemInform Abstract: β‐Ketoesters Derived from Pyroglutamic Acid: New Entry to Hydroxylated Pyrrolizidinones.

Bouc

Thomassigny

Greck

2009

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Toward Pyridine–Heterocycle Patterns through Prins and Aza‐Prins Cyclisations: Application to a Short Synthesis of (±)‐Anabasine

et al. 2014

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The formation of pyridine‐containing bisheterocycles through a Prins‐type cyclisation is described. Pyridine–tetrahydropyran and pyridine–piperidine conjugates could be efficiently obtained using various carbaldehydes including dicarbaldehydes, and either homoallylic alcohols or a homoallylic amine. Selective partial or complete hydrogenation led to new bisheterocycle combinations. A two‐step sequence involving an aza‐Prins cylisation allowed us to prepare the alkaloid anabasine.

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b-Ketoesters Derived from Pyroglutamic Acid: New Entry to Hydroxylated Pyrrolizidinones

Cited by 2 publications

References 17 publications

ChemInform Abstract: β‐Ketoesters Derived from Pyroglutamic Acid: New Entry to Hydroxylated Pyrrolizidinones.

ChemInform Abstract: β‐Ketoesters Derived from Pyroglutamic Acid: New Entry to Hydroxylated Pyrrolizidinones.

Toward Pyridine–Heterocycle Patterns through Prins and Aza‐Prins Cyclisations: Application to a Short Synthesis of (±)‐Anabasine

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