One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

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One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

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 gene...

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One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues† †Electronic supplementary information (ESI) available: Experimental details. Preparation of NCS enzymes, reaction details, compound characterization and analytical details. See DOI: 10.1039/c7cc08024g

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 gene...

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ژورنال

عنوان ژورنال: Chemical Communications

سال: 2018

ISSN: 1359-7345,1364-548X

DOI: 10.1039/c7cc08024g