1253265-72-3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 864967-32-8 (3R,8R,8aR)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 1253265-22-3 (3R,8S,8aR)-8-allyl-6-(tert-butoxycarbonyl)-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 1253265-24-5 (3R,7S,8S,8aR)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 

Relevant academic research and scientific papers

Total synthesis of (+)-madangamine D

Madangamines are a group of bioactive marine sponge alkaloids, embodying an unprecedented diazapentacyclic skeletal type. The enantioselective total synthesis of madangamine D has been accomplished, and represents the first total synthesis of an alkaloid of the madangamine group. It involves the stereoselective construction of the diazatricyclic ABC core using a phenylglycinol-derived lactam as the starting enantiomeric scaffold and the subsequent assembly of the peripheral macrocyclic rings. The synthesis provides, for the first time, a pure sample of madangamine D and confirms the absolute configuration of this alkaloid family.

First enantioselective synthesis of the diazatricyclic core of madangamine alkaloids

En route to madangamines: A unified strategy has been developed for the enantioselective assembly of functionalized diazatricyclic synthetic precursors of madangamines (see scheme; Bn=benzyl, Boc=tert-butoxycarbonyl, Mbs=paramethoxybenzenesulfonyl).