Synthesis of (–)-Bulgecinine and 5-epi-Bulgecinine through Proline-Catalysed Asymmetric α-Hydroxylation of an Aldehyde Derived from l-Glutamic Acid

Vipin Kumar Jain; Mrityunjay Kumar

doi:10.1055/s-0039-1690332

SynOpen, Inhaltsverzeichnis

CC BY-ND-NC 4.0 · SynOpen 2019; 03(04): 96-102
DOI: 10.1055/s-0039-1690332

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Synthesis of (–)-Bulgecinine and 5-epi-Bulgecinine through Proline-Catalysed Asymmetric α-Hydroxylation of an Aldehyde Derived from l-Glutamic Acid

Vipin Kumar Jain∗

,

Mrityunjay Kumar

Abstract

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Abstract

A very efficient synthetic route to (–)-bulgecinine and 5-epibulgecinine from an aldehyde derived from l-glutamic acid is reported. Proline-catalysed asymmetric α-hydroxylation reaction of an aldehyde is the key step in this synthesis, which is used to incorporate a hydroxyl group at the α-position to that aldehyde in good yield and with very high diastereoselectivity. Both (–)-bulgecinine and 5-epi-bulgecinine are synthesised from the same olefin via epoxidation followed by BF₃·OEt₂-catalyzed intramolecular cyclisation. This synthetic route can easily be extended for the synthesis of the enantiomer and other isomers of bulgecinine starting from an aldehyde derived from d-glutamic acid.

Key words

asymmetric hydroxylation - organocatalysis - diastereoselectivity - glycopeptide - antibiotics

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