One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

Jianxiong Zhao; Benjamin R. Lichman; John M. Ward; Helen C. Hailes

doi:10.1039/c7cc08024g

One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

Jianxiong Zhao, Benjamin R. Lichman, John M. Ward, Helen C. Hailes^*

^*Corresponding author for this work

Biology

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1323-1326
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	11
DOIs	https://doi.org/10.1039/c7cc08024g
Publication status	Published - 1 Jan 2018

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©The Royal Society of Chemistry 2018

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c7cc08024g
©The Royal Society of Chemistry 2018
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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.",

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AU - Lichman, Benjamin R.

AU - Ward, John M.

AU - Hailes, Helen C.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - 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.

AB - 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.

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JO - Chemical Communications

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One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues

Abstract

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