Issue 6, 2017

Enantioselective synthesis of naturally occurring isoquinoline alkaloids: (S)-(−)-trolline and (R)-(+)-oleracein E

Abstract

The highly efficient asymmetric syntheses of a pair of enantiomers, (S)-(−)-trolline and (R)-(+)-oleracein E, from commercially available 2-methyl-3-butyn-2-ol, benzaldehyde and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline have been achieved in five steps with the catalytic enantioselective C1-alkynylation of 6,7-dimethoxy-3,4-dihydroisoquinoline as a key step, providing an efficient general approach for this type of naturally occurring chiral isoquinoline alkaloids.

Graphical abstract: Enantioselective synthesis of naturally occurring isoquinoline alkaloids: (S)-(−)-trolline and (R)-(+)-oleracein E

Supplementary files

Article information

Article type
Research Article
Submitted
22 jan 2017
Accepted
04 mar 2017
First published
06 mar 2017
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2017,4, 958-966

Enantioselective synthesis of naturally occurring isoquinoline alkaloids: (S)-(−)-trolline and (R)-(+)-oleracein E

W. Lin and S. Ma, Org. Chem. Front., 2017, 4, 958 DOI: 10.1039/C7QO00062F

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