- Three-Step Catalytic Asymmetric Total Syntheses of 13-Methyltetrahydroprotoberberine Alkaloids
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(S,R)-N-PINAP was identified to be the chiral ligand for highly enantioselective CuI-catalyzed reaction of tetrahydroisoquinolines (THIQs), alkynes, and 2-bromobenzaldehyde derivatives. This enables us to accomplish the first asymmetric total synthesis of 12 natural 13-methyltetrahydroprotoberberine (13-MeTHPB) alkaloids in only three catalytic steps with 47-64% overall yields. In addition, the Pd-catalyzed reductive Heck cyclization was successfully extended to three Pd-catalyzed domino reactions (Heck/Suzuki, Heck/Sonogashira, and Heck/Heck), which greatly expands the synthetic utility of this catalytic strategy and allows expeditious access to 13-substituted tetrahydroprotoberberines for further bioactivity evaluation.
- Zhou, Shiqiang,Tong, Rongbiao
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p. 1594 - 1597
(2017/04/13)
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- THE BIOSYNTHESIS OF THE ALKALOIDS OF CORYDALIS MEIFOLIA WALL.
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Tracer experiments show that corlumine, cavidine and yenhusomine are stereospecifically biosynthesized from (R)-(-)-reticuline.
- Bhakuni, Dewan S.,Jain, Sudha,Gupta, Sandeep
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p. 675 - 680
(2007/10/02)
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- Absolute Configurations of the cis- and trans-13-Methyltetrahydroprotoberberines. Total Synthesis of (+)-Thalictricavine, (+)-Canadine, (+/-)-, (-)-, and (+)-Thalictrifoline, and (+/-)-, (-)-, and (+)-Cavidine
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The tetrahydroprotoberberine alkaloids (+)-thalictricavine and (+)-canadine have been synthesized from an optically resolved (+)-13-carboxy-7,8,13,14-tetrahydro-9-oxoprotoberberine .This establishes the absolute configuration of (+)-thalictricavine as 13S,14R. (+)-Thalictrifoline and (+)-cavidine have also been prepared from a common intermediate, (+)-32, whose absolute configuration was established by correlation with (+)-26.This determines the absolute configuration of (+)-thalictrifoline as 13R,14R, of (+)-corydalic acid methyl ester (22) as 3R,4R, and of the protopine (+)-corycavine (20) as 13R.
- Iwasa, Kinuko,Gupta, Yash Pal,Cushman, Mark
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p. 4744 - 4750
(2007/10/02)
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