29550-24-1

Upstream product

• 78982-17-9 Methanesulfonic acid (13S,13aR)-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-13-ylmethyl ester 
• 94143-83-6 5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 53811-50-0 6-bromo-2,3-dimethoxybenzaldehyde 
• 2220-12-4 dehydrothalictricavine iodide 
• 79027-74-0 (+)-cis-2,3-(Methylenedioxy)-8-oxo-9,10-dimethoxy-13-(methoxycarbonyl)tetrahydroprotoberberine 
• 79082-06-7 (+)-cis-2,3-(Methylenedioxy)-9,10-dimethoxy-13-(hydroxymethyl)tetrahydroprotoberberine 
• 79027-72-8 (+)-cis-2,3-(Methylenedioxy)-8-oxo-9,10-dimethoxy-13-carboxytetrahydroprotoberberine 

Downstream Products

• 518-69-4 corydaline 

Relevant academic research and scientific papers

Three-Step Catalytic Asymmetric Total Syntheses of 13-Methyltetrahydroprotoberberine Alkaloids

(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.

UTILIZATION OF PROTOPINE AND RELATED ALKALOIDS.XVIII. SOME REACTIONS OF ANHYDROISODIHYDROCORYCAVIDINE AND ITS N-OXIDE

Hydroxylation of anhydroisodihydrocorycavidine 4 with osmium tetroxide affords the α-glycol 7 and the 13,14-seco keto aldehyde 8.Treatment of the N-oxide 6 with acetic anhydride/acetic acid gives the 7,8-seco diacetate 10 and the indene acetate 11.The for

Absolute Configurations of the cis- and trans-13-Methyltetrahydroprotoberberines. Total Synthesis of (+)-Thalictricavine, (+)-Canadine, (+/-)-, (-)-, and (+)-Thalictrifoline, and (+/-)-, (-)-, and (+)-Cavidine

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.