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One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

Zhao, J; Lichman, BR; Ward, JM; Hailes, HC; (2018) One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues. Chemical Communications , 54 (11) pp. 1323-1326. 10.1039/c7cc08024g. Green open access

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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.

Type: Article
Title: One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues
Location: England
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c7cc08024g
Publisher version: http://dx.doi.org/10.1039/c7cc08024g
Language: English
Additional information: This journal is © The Royal Society of Chemistry 2018. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > Div of Biosciences
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science > Dept of Biochemical Engineering
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/10041699
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