55785-30-3

Upstream product

• 27766-71-8 (±)-(2R*,4aS*,5R*,8aR*)-decahydro-5-methyl-2-propylquinoline 
• 142003-72-3 (2S,4aS,8aR)-1-Benzyl-2-propyl-2,4a,8,8a-tetrahydro-1H-quinolin-7-one 
• 142003-59-6 (2S^*,4aS^*,5S^*,8aR^*)-1-benzyl-2-(1-propyl)-(Δ-3,4)-5-methyl-(Δ-6,7)-7-<(trifluoromethanesulfonyl)oxy>hexahydroquinoline 

Relevant academic research and scientific papers

Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products

Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

Stereospecific Total Syntheses of Decahydroquinoline Alkaloids (+/-)-195A and (+/-)-2-epi-195A

The total syntheses of decahydroquinoline alkaloids (+/-)-195A (pumiliotoxin C) and (+/-)-2-epi-195A are described.An unexpected, stereospecific epimerization of the C2 stereocenter of intermediate 6a occurred during its reduction.The isomerization result