1206607-95-5

Upstream product

• 1027172-71-9 (5S)-6-((S)-1,2,3,5,6,8a-hexahydroindolizine-8-carbonyl)-5-methylcyclohex-2-enone 
• 76-05-1 trifluoroacetic acid 
• 1378306-84-3 (5S,6R)-6-((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-1,2,5,6-tetrahydropyridine-3-carbonyl)-5-methylcyclohex-2-enone 
• 1378306-79-6 (S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-1,2,5,6-tetrahydropyridine-3-carbaldehyde 
• 1378307-10-8 ((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-1,2,5,6-tetrahydropyridin-3-yl)methanol 
• 1378307-09-5 C₂₂H₄₃NO₄SSi 
• 1378306-83-2 (S)-N-(but-3-en-1-yl)-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide 
• 130418-90-5 (S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate 
• 69610-41-9 Boc-L-Pro-H 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 1312994-82-3 (S)-(1,2,3,5,6,8a-hexahydroindolizin-8-yl)methanol 
• 1312994-85-6 (S)-methyl 1,2,3,5,6,8a-hexahydroindolizine-8-carboxylate 
• 1312994-81-2 (S)-S-ethyl 1,2,3,5,6,8a-hexahydroindolizine-8-carbothioate 
• 1312994-79-8 (S)-1-(3,3-diethoxypropyl)-2-(ethylthioethynyl)pyrrolidine 

Relevant academic research and scientific papers

A versatile enantioselective synthesis of azabicyclic ring systems: A concise total synthesis of (+)-grandisine D and unnatural analogues

Closing in on azacines: We have developed a new six step approach for the rapid and enantioselective synthesis of indolizidine, pyrrolo[1,2-a]azepine, and pyrrolo[1,2-a]azocine azabicyclic systems and their respective lactam congeners, which are found in a host of natural products as well as pharmaceutical preparations. This protocol enables a concise enantioselective total synthesis of (+)-grandisine D in 16.4 % overall yield from commercial materials (see scheme). Copyright

The preparation of (-)-grandisine B from (+)-grandisine D; A biomimetic total synthesis or formation of an isolation artefact?

An efficient new alkyne-acetal cyclization procedure has been developed to prepare enantiopure indolizidine building blocks from l-proline and then applied to prepare the Elaeocarpus-derived alkaloids grandisine B and grandisine D in an efficient manner.

Total synthesis of grandisine d

Total synthesis of grandisine D (5) was achieved by a Bronsted acid mediated Morita-Baylis-Hillman (MBH) ring-closure reaction and stereoselective aldol condensation with (S)-5-methylcyclohexenone (9) as key steps. The MBH approach was also applicable for