CC BY-ND-NC 4.0 · SynOpen 2019; 03(04): 96-102
DOI: 10.1055/s-0039-1690332
paper
Copyright with the author(s) (2019) The author(s)

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
V.K.J. thanks CSIR - Indian Institute of Chemical Biology for a Senior Research Fellowship
Further Information

Publication History

Received: 20 August 2019

Accepted after revision: 12 September 2019

Publication Date:
09 October 2019 (online)

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.

Supporting Information

 
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