1428872-64-3

Upstream product

• 1428872-53-0 (4R,4aR,6S,7S,8aS)-7-(benzyloxy)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline 
• 1428872-52-9 (4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline 
• 864967-37-3 (3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline 
• 18719-24-9 oct-7-enoic acid 
• 101639-95-6 oct-7-enoyl chloride 
• 1428872-54-1 (4R,4aR,6S,7S,8aS)-7-(benzyloxy)-4-[3-(1,3-dioxolan-2-yl)propyl]-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline 
• 1428872-47-2 (3R,6R,6aR,10aS,10bR)-6-[3-(1,3-dioxolan-2-yl)propyl]-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[3,2-a]isoquinoline 
• 1428872-55-2 (4R,4aR,6S,7S,8aS)-7-(benzyloxy)-4-[3-(1,3-dioxolan-2-yl)propyl]-6,4-(iminomethano)-2-(7-octenoyl)-9-(p-toluenesulfonyl)perhydroisoquinoline 

Downstream Products

• 1428872-59-6 C₂₈H₄₂N₂O₄S 
• 1428872-56-3 (4R,4aR,6S,7S,8aS)-7-(benzyloxy)-6,4-(iminomethano)-2-(7-octenoyl)-4-(4-pentenyl)-9-(p-toluenesulfonyl)perhydroisoquinoline 

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 tetracyclic intermediates en route to madangamine D

The enantioselective synthesis of advanced tetracyclic precursors of madangamine D, bearing rings ABCD of this alkaloid, is reported. The saturated 14-membered ring is assembled from functionalized diazatricyclic intermediates following either ring-closin