1428470-93-2

Upstream product

• 533-31-3 Sesamol 
• 1428471-06-0 (2S,3R)-tert-butyl 2-benzylamino-3-(2-hydroxy-4,5-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)propanoate 
• 1428470-79-4 (R)-tert-butyl 3-(4,5-methylenedioxy-2-vinylphenyl)-3-(3,4,5-trimethoxyphenyl)propanoate 
• 1428470-87-4 (R)-tert-butyl 3-[4,5-methylenedioxy-2-(trifluoromethanesulfonyloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)propanoate 
• 1428470-86-3 (R)-tert-butyl 3-(2-hydroxy-4,5-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)propanoate 

Relevant academic research and scientific papers

Enantioselective formal synthesis of (-)-podophyllotoxin from (2 S,3 R)-3-arylaziridine-2-carboxylate

Meyers' 4-aryl-1-tetralone-lactone and ent-Zhang's 2-diarylmethyl-4- oxobutanoate were synthesized in the formal synthesis of (-)-podophyllotoxin from (2S,3R)-3-arylaziridine-2-carboxylate, via 3,3-diarylpropanoate as a common intermediate, in an overall 42% yield through 10 steps and 31% yield through 6 steps, respectively. The key steps in the synthesis were regio- and diastereoselective ring opening with an aromatic nucleophile, samarium iodide promoted reductive C-N bond cleavage, and Stille coupling for introducing the vinyl functionality. The starting aziridine was enantioselectively prepared from 3,4,5-trimethoxybenzaldehyde by guanidinium ylide mediated asymmetric aziridination. All nitrogen components used in the reaction sequence are reusable as the starting guanidinium source.