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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.

SUBMITTER: Zhao J

PROVIDER: S-EPMC5804477 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues.

Zhao Jianxiong J Lichman Benjamin R BR Ward John M JM Hailes Helen C HC

Chemical communications (Cambridge, England) 20180201 11

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. ...[more]

PMID: 29345260

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