386761-70-2

Upstream product

• 115887-36-0 (4R)-4-(benzyloxy)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)butan-1-ol 
• 100-39-0 benzyl bromide 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 87604-46-4 (2R,3R)-1,2-O-isopropylidene-5-hexene-1,2,3-triol 
• 87604-54-4 (R)-4-((R)-1-(benzyloxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 386761-60-0 (4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol 
• 386761-61-1 (4R)-4-[(1R,4S)-4-azido-1-(benzyloxy)hept-6-enyl]-2,2-dimethyl-1,3-dioxolane 

Relevant academic research and scientific papers

Enantioselective allyltitanations and metathesis reactions. Application to the synthesis of piperidine alkaloids (+)-sedamine and (-)-prosophylline

An enantioselective synthesis of the piperidine alkaloids (+)-sedamine and (-)-prosophylline is reported. The synthesis of (+)-sedamine has been achieved in 12 steps with an overall yield of 20% from benzaldehyde, and (-)-prosophylline was obtained in 15 steps with an overall yield of 9.2%, starting from D-glyceraldehyde acetonide 14. The key steps are enantioselective allyltitanation reactions and ring-closing or cross-metathesis reactions.

Enantioselective allyltitanation and cross-metathesis. Synthesis of (-)-prosophylline

An enantioselective synthesis of (-)-prosophylline has been accomplished in 15 steps from protected D-glyceraldehyde, with an overall yield of 9.2%, by using two enantioselective allyltitanations and a cross-metathesis reaction as the key-steps.