Abstract
One-pot, one-substrate, triangular chemoenzymatic cascades featuring transaminase (TAm) and norcoclaurine synthase (NCS) enables the formation of (S)-benzylisoquinoline and (S)-tetrahydroprotoberberine alkaloids.
Highlights
In order to minimise waste products and reduce the usage of finite resources, chemistry must find ‘green’ alternatives to traditional synthetic methods.[1]
A key step in the synthesis of many of these compounds is the formation of the tetrahydroisoquinoline (THIQ) moiety via a Pictet–Spengler condensation.[10]
There has been recent progress made in the enzymatic synthesis of diverse chiral THIQs using the plant enzyme norcoclaurine synthase (NCS).[12]
Summary
One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine†. We describe novel chemoenzymatic routes to (S)-benzylisoquinoline and (S)-tetrahydroprotoberberine alkaloids using the enzymes transaminase (TAm) and norcoclaurine synthase (NCS) in a onepot, one-substrate ‘triangular’ cascade. Employment of up to two C–C bond forming steps allows for the rapid generation of molecular complexity under mild conditions
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