892858-52-5

Upstream product

• 892858-48-9 6-((E)-3-bromo-1-propenyl)-5-methoxycarbonyl-benzo[1,3]dioxole 
• 100-46-9 benzylamine 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 

Downstream Products

• 892858-54-7 (3R,4S,4aR,11bR)-5-benzyl-3,4-isopropylidenedioxy-3,4a,5,11b-tetrahydro-4H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 

Relevant academic research and scientific papers

Synthesis of 7-deoxypancratistatin from carbohydrates by the use of olefin metathesis

The stereocontrolled synthesis of (+)-7-deoxypancratistatin is described. The convergent synthesis has been achieved by two different strategies, both of which commence from a pentose and piperonal. The latter is converted into allylic bromide 7, which is then coupled with a protected methyl 5-deoxy-5-iodo-D-ribofuranoside in the presence of zinc metal. The first strategy involves a total of only 13 steps from D-ribose and piperonal, but suffers from a low yield in the zinc-mediated reaction between ribofuranoside 9, benzylamine, and bromide 7.The second strategy involves a total of 18 steps from D-xylose and piperonal. The former is converted into ribofuranoside 28, which is coupled with bromide 7 in the presence of zinc, and this is followed by ring-closing olefin metathesis. Subsequent Overman rearrangement, dihydroxylation. and deprotection then affords the natural product.