58117-91-2

Upstream product

• 1040735-85-0 (2S,4aS,5R,8aR)-1-(tert-butoxycarbonyl)-5-methyl-2-propyldecahydroquinoline 
• 27766-71-8 (±)-(2R*,4aS*,5R*,8aR*)-decahydro-5-methyl-2-propylquinoline 
• 160798-31-2 (2R,4aR,5S)-5-Benzyloxy-2-ethyl-2,4a,5,6,7,8-hexahydropyrido<1,2-b><1,2>oxazin-8-one 
• 160728-63-2 (2R,3S,6S)-1-Benzoyl-3-benzyloxy-2-<(3R)-3-hydroxypentyl>-6-propylpiperidine 
• 160728-56-3 (4E,6E,3S)-3-Benzyloxynona-4,6-dienyl toluene-p-sulfonate 
• 160728-65-4 (2R,6S)-1-Benzoyl-2-(3-oxopentyl)-6-propylpiperidine-3-one 
• 160728-64-3 (2R,3S,6S)-1-Benzoyl-2-<(3R)-3-hydroxypentyl>-6-propylpiperidine-3-ol 
• 160728-72-3 (2S,4aS,5S,8aR)-1-Benzyl-5-methyl-2-propylspiro 
• 160728-68-7 (2S,4aS,5R,8aR)-1-Benzoyl-5-methyl-2-propyldecahydroquinolin-6-one 
• 160728-67-6 (2S,8aR)-1-Benzoyl-5-methyl-2-propyl-1,2,3,4,6,7,8,8a-octahydroquinolin-6-one 
• 160728-61-0 (2R,4aR,5S)-5-Benzyloxy-2-ethyl-2,3,4,4a,5,6,7,8-octahydropyrido<1,2-b><1,2>oxazin-8-one 
• 164672-08-6 (2R,3S,6S)-3-Benzyloxy-2-<(3R)-3-hydroxypentyl>-6-propylpiperidine 
• 160728-60-9 (5E,7E,4S)-4-Benzyloxy-N-hydroxyocta-5,7-dienamide 

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.

Biomimetic construction of the hydroquinoline ring system. Diastereodivergent enantioselective synthesis of 2,5-disubstituted cis -decahydroquinolines

Figure presented The straightforward enantioselective construction of the hydroquinoline ring system from 1,5-polycarbonyl derivatives, using (R)-phenyglycinol as a chiral latent form of ammonia, is reported. The process mimics the key steps believed to o

A biomimetic enantioselective approach to the decahydroquinoline class of dendrobatid alkaloids

(Chemical Equation Presented) A princely synthesis: The hypothetical key step in the biosynthesis of the decahydroquinoline dendrobatid alkaloids, such as cis-195 A found in frogs, from 1,5-polycarbonyl derivatives is mimicked by using (R)-phenylglycinol as a chiral latent form of ammonia in a double cyclocondensation reaction.

Stereoselective total synthesis of (-)-pumiliotoxin C by an aqueous intramolecular acylnitroso Diels-Alder approach

A chiral approach to (-)-pumiliotoxin C based on an aqueous intramolecular acylnitroso Diels-Alder reaction is described. Upon treatment of the (S)-1,3-diene hydroxamic acid 19, available from L-malic acid, with Pr4NIO4 under the aqu

Ruthenium-Catalyzed Hydration of Nitriles and Transformation of δ-Ketonitriles to Ene-lactams: Total Synthesis of (-)-Pumiliotoxin C

Hydration of nitriles with 1-2 equivalents of water can be performed efficiently by using RuH2(PPh3)4 catalyst to give the corresponding amides.Under the similar reaction conditions, δ-ketonitriles can be converted into the corresponding ene-lactams, which are versatile synthetic intermediates.The efficiency of the reaction is demonstrated by the short-step synthesis of (-)-pumiliotoxin C.