79808-95-0

Upstream product

• 79808-93-8 (+/-)-N-formyl-N-demethyl-18-methylenevallesamidine 
• 82359-78-2 (-)-(2S,7R,20R,21R)-1-formyl-1-demethyl-18-methylenevallesamidine 
• 6243-54-5 2-indol-3-ylethyl toluene-p-sulphonate 

Relevant academic research and scientific papers

Concise syntheses of eburnane indole alkaloids

The asymmetric divergent syntheses of a group of C20 ethyl oxo-functionalized eburnane alkaloids, (-)-eburnaminol (5), (+)-larutenine (6), (-)-terengganensine B (7), (-)-strempeliopine (8), and (-)-terengganensine A (9), have been achieved. The key step in the assembly of the complex ring system of the target molecules is a photoredox catalytic nitrogen-centered radical cascade reaction, which allows the regioselective and stereoselective construction of the B, C, and D rings and the installation of the C21 chirality of the eburnane alkaloid skeleton in one pot.

ABSOLUTE CONFIGURATION OF (-)-STREMPELIOPINE

The (-)-strempeliopine was assigned the absolute configuration depicted in I on the basis of its stereospecific synthesis from (+)-18-methylenevincadifformine (II).

The total synthesis of (-) -strempeliopine: Via palladium-catalyzed decarboxylative asymmetric allylic alkylation

In the work reported herein, the concise and enantioselective total synthesis of the Schizozygine alkaloid (-)-strempeliopine was developed. This synthetic strategy featured the palladium-catalyzed decarboxylative asymmetric allylic alkylation of N-benzoy

Total Synthesis of (-)-Strempeliopine

A total synthesis of (-)-strempeliopine is disclosed that enlists a powerful SmI2-mediated and BF3·OEt2-initiated dearomative transannular radical cyclization onto an indole by an N-acyl α-aminoalkyl radical that is derived by single electron reduction of an in situ generated iminium ion for formation of a quaternary center and the strategic C19-C2 bond in its core structure.

Application of cross-conjugated heteroaromatic betaines to the synthesis of the schizozygane alkaloid (±)-strempeliopine

(Chemical Equation Presented) An efficient stereocontrolled route to the isoschizozygane alkaloid core has been developed utilizing an intramolecular 1,4-dipolar cycloaddition of a cross-conjugated heteroaromatic betaine. The resulting cycloadduct undergo

(-)-STREMPELIOPINE. STEREOSELECTIVE TOTAL SYNTHESIS AND THE DETERMINATION OF ABSOLUTE CONFIGURATION

A synthesis of (+/-)-strempeliopine (II) is described, the key step of which is the stereoselective reductive rearrangement of 18-methylene-1,2-dehydroaspidospermidine (XI).The absolute configuration of the natural (-)-base II was determined as (2S,7R,20R,21R) on the basis of the synthesis from (+)-18-methylenevincadifformine (XVII) the configuration of which was derived from a comparison of circular dichroism properties of bases with a β-anilinoacrylate chromophore.The biogenesis of the alkaloids of the schizozygane type is discussed.

STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-STREMPELIOPINE

The 18-methylene-1,2-dehydroaspidospermidine (III) was stereospecifically transformed into the schizozygane alkaloid strempeliopine (II) in 16,6 percent overall yield.