Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile.

doi:10.1021/jo201871c

Paper

Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile.

Published Oct 26, 2011 · Nancy Blank, T. Opatz

The Journal of organic chemistry

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40

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0

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Abstract

Under controlled conditions, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile can be quantitatively deprotonated in the α-position. Its alkylation directly furnishes 3,4-dihydroisoquinolines which can serve as starting materials for the preparation of various alkaloids. Here, the preparation of the benzylisoquinolines (+)-laudanidine, (+)-armepavine, and (+)-laudanosine as well as the tetrahydroprotoberberines (-)-corytenchine and (-)-tetrahydropseudoepiberberine using Noyori's asymmetric transfer hydrogenation are described. The dimeric alkaloids (+)-O-methylthalibrine and (+)-tetramethylmagnolamine were obtained from nonracemic precursors in Ullmann diaryl ether syntheses.

Study Snapshot

This study presents a method for enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from deprotonated -aminonitrile, with potential applications in pharmaceutical and biotechnology fields.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile.

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References

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Diaryl ether formation is crucial for the synthesis of natural products, with various synthetic methods and successful applications shown in a table.

Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step.

This study presents a new route to tetrahydroisoquinoline alkaloids, enabling the synthesis of (+/-)-carnegine, (+/-)-norlaudanosine, and (+/-)-O,O-dimethylcoclaurine.

Enantioselective total synthesis and X-ray structures of the tetrahydroprotoberberine alkaloids (-)-(S)-tetrahydropalmatrubine and (-)-(S)-corytenchine.

This study reports the first enantioselective total synthesis and X-ray structures of (S)-tetrahydropalmatrubine and (S)-corytenchine, both derived from (S)-N-norlaudanidine, using a chiral

Citations

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Recent advances in total synthesis of protoberberine and chiral tetrahydroberberine alkaloids.

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Three synthesized alkaloids show promising druglike potential for treating Chagas disease, potentially through inhibition of kinetoplast division.

Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020)

Recent advancements in total synthesis of tetrahydroisoquinoline alkaloids, using novel synthetic design and modern chemical methodology, have shown promise for their therapeutic potential.

Recent advances in oxidative phenol coupling for the total synthesis of natural products.

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The biology and total syntheses of bisbenzylisoquinoline alkaloids.

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This study developed a greener strategy for producing high-value THPBs in engineered Escherichia coli, enabling further pharmaceutical research with limited product quantity.