Issue 11, 2018

One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

Abstract

Chemoenzymatic reaction cascades can provide access to chiral compounds from low-cost starting materials in one pot. Here we describe one-pot asymmetric routes to tetrahydroisoquinoline alkaloids (THIAs) using the Pictet–Spenglerase norcoclaurine synthase (NCS) followed by a cyclisation, to give alkaloids with two new heterocyclic rings. These reactions operated with a high atom economy to generate THIAs in high yields.

Graphical abstract: One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

Supplementary files

Article information

Article type
Communication
Submitted
26 Oct 2017
Accepted
30 Nov 2017
First published
18 Jan 2018
This article is Open Access
Creative Commons BY license

Chem. Commun., 2018,54, 1323-1326

One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

J. Zhao, B. R. Lichman, J. M. Ward and H. C. Hailes, Chem. Commun., 2018, 54, 1323 DOI: 10.1039/C7CC08024G

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