263025-37-2

Upstream product

• 179686-58-9 N-[(1,1-dimethylethoxy)carbonyl]-N-(3-oxobutyl)glycine ethyl ester 
• 129228-72-4 (3-oxo-butylamino)-acetic acid ethyl ester 
• 263025-19-0 3-hydroxy-3-methyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-ethyl ester 

Downstream Products

• 148717-88-8 (1S,5aR,12aS,13aS)-rel-2,3,11,12,12a,13-hexahydro-14-methoxy-1,12,12-trimethyl-5H,6H-5a,13a-(iminomethano)-1H-indolizino[7,6-b]carbazol-14-one 
• 148717-88-8 (1R,5aR,12aS,13aS)-rel-2,3,11,12,12a,13-hexahydro-14-methoxy-1,12,12-trimethyl-5H,6H-5a,13a-(iminomethano)-1H-indolizino[7,6-b]carbazol-14-one 
• 148717-88-8 (1R,5aR,12aR,13aS)-rel-2,3,11,12,12a,13-hexahydro-14-methoxy-1,12,12-trimethyl-5H,6H-5a,13a-(iminomethano)-1H-indolizino[7,6-b]carbazol-14-one 

Relevant academic research and scientific papers

Total synthesis of VM55599. Utilization of an intramolecular Diels-Alder cycloaddition of potential biogenetic relevance

The total synthesis of VM55599, a natural metabolite of Penicillium sp. IMI332995, has been achieved via an intramolecular Diels-Alder cycloaddition of a reverse isoprene moiety across an azadiene system. The diastereoselectivity of the intramolecular Diels-Alder cycloaddition has biogenetic implications and is discussed in the context of the biogenetic relationship of VM55599 to the paraherquamides.