42460-99-1

Upstream product

• 252206-78-3 C₁₉H₁₈N₂O₃ 
• 73-22-3 L-Tryptophan 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1024014-00-3 tert-butyl 3-({(3′S,8a′S)-2′-(4′′-methoxybenzyl)-octahydro-1′,4′-dioxopyrrolo[1,2-a]pyrazin-3′-yl}methyl)-1H-indole-1-carboxylate 
• 1447950-15-3 N-(tert-butoxycarbonyl)-N-(4-methoxybenzyl)-L-tryptophanyl-L-proline methyl ester 
• 1447950-18-6 C₂₄H₂₅N₃O₃ 
• 1357154-79-0 C₄₀H₄₅N₃O₅S 
• 1447950-12-0 N-(tert-butoxycarbonyl)-N-(4-methoxybenzyl)-L-tryptophan 

Relevant academic research and scientific papers

The cascade radical cyclisation approach to prenylated alkaloids: Synthesis of stephacidin A and notoamide B

A strategy for the synthesis of members of the prenylated indole alkaloid family is described, which involves a radical cascade process of an appropriately substituted diketopiperazine (DKP) core structure. Several approaches to the generation of the initial radical were explored, with the most successful involving treatment of a sulfenyl substituted DKP under classical reductive conditions by heating with Bu3SnH and a radical initiator. The required, fully substituted, radical precursor DKP structures were prepared using regio- and stereocontrolled enolate chemistry of simpler proline-tryptophan derived DKPs. The new approach allowed rapid access to a key polycyclic indoline structure, which was converted into either of the natural products stephacidin A or notoamide B.