A Direct Route to Erythrinanes v i a α-Amidoalkylation, Conjugate Addition and Ring-Closing Metathesis Reactions

Inaki      Osante; Nuria      Sotomayor; Esther      Lete

doi:10.2174/1570178043400712

Abstract

A direct route to erythrinanes has been completed by a sequence that involves diastereoselective conjugate addition on a α,β-unsaturated lactam, followed by a ring-closing metathesis reaction to construct ring A. The synthesis of the key intermediates C-10b functionalized dihydropyrroloisoquinolines is achieved via Parham cyclisation and α-amidoalkylation reactions.

Keywords: erythrina alkaloids, amidoalkylation, conjugate addition, lithiation, ring-closing metathesis

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Letters in Organic Chemistry

Title: A Direct Route to Erythrinanes v i a α-Amidoalkylation, Conjugate Addition and Ring-Closing Metathesis Reactions

Volume: 1 Issue: 4

Author(s): Inaki Osante, Nuria Sotomayor and Esther Lete

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Keywords: erythrina alkaloids, amidoalkylation, conjugate addition, lithiation, ring-closing metathesis

Abstract: A direct route to erythrinanes has been completed by a sequence that involves diastereoselective conjugate addition on a α,β-unsaturated lactam, followed by a ring-closing metathesis reaction to construct ring A. The synthesis of the key intermediates C-10b functionalized dihydropyrroloisoquinolines is achieved via Parham cyclisation and α-amidoalkylation reactions.

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Osante Inaki, Sotomayor Nuria and Lete Esther, A Direct Route to Erythrinanes v i a α-Amidoalkylation, Conjugate Addition and Ring-Closing Metathesis Reactions, Letters in Organic Chemistry 2004; 1 (4) . https://dx.doi.org/10.2174/1570178043400712