154569-07-0

Basic information

• Product Name: (2S,4aS,5R,8aR)-N-phenoxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one
• CAS NO: 154569-07-0
• Molecular Weight: 329.439
• Mol File: 154569-07-0.mol

Chemical Properties

• CAS DataBase Reference: (2S,4aS,5R,8aR)-N-phenoxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4aS,5R,8aR)-N-phenoxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one(154569-07-0)
• EPA Substance Registry System: (2S,4aS,5R,8aR)-N-phenoxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one(154569-07-0)

Safety Data

• Hazardous Substances Data: 154569-07-0(Hazardous Substances Data)

Upstream product

• 154569-06-9 (2S,8aR)-N-phenoxycarbonyl-2-propyl-4a,5-didehydro-quinolin-4-one 
• 917-54-4 methyllithium 
• 1885-14-9 phenyl chloroformate 
• 154569-09-2 (2S,4aR,5R,8aR)-N-phenoxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one 
• 217447-16-0 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-((2R,6S)-4-oxo-2-pent-4-enyl-6-propyl-piperidin-1-yl)-tetrahydro-pyran-3-yl ester 
• 138832-06-1 (R)-4-Oxo-2-pent-4-enyl-3,4-dihydro-2H-pyridine-1-carboxylic acid phenyl ester 
• 154467-62-6 (R)-4-Oxo-2-pent-4-enyl-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 154569-05-8 (2R,6S)-4-Oxo-2-(4-oxo-butyl)-6-propyl-piperidine-1-carboxylic acid phenyl ester 
• 154569-04-7 (2R,6S)-4-Oxo-2-pent-4-enyl-6-propyl-piperidine-1-carboxylic acid phenyl ester 
• 144375-66-6 4-Methoxy-1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride 
• 154467-63-7 (R)-2-Pent-4-enyl-2,3-dihydro-1H-pyridin-4-one 
• 217447-19-3 (2S,8aR)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-propyl-4a,5-didehydro-decahydroquinolin-4-one 
• 217447-18-2 (2R,6S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(4-oxo-butyl)-6-propyl-piperidin-4-one 
• 217447-15-9 (2R)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(4-pentenyl)-5,6-didehydropiperidin-4-one 

Downstream Products

• 154569-08-1 (2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester 
• 27766-71-8 (-)-pumiliotoxin C 

Relevant articles and documents

Carbohydrate auxiliaries in stereoselective syntheses of decahydroquinoline alkaloids

Using tetra-O-pivaloyl-β-D-galactopyranosylamine as the chiral auxiliary, both trans- and cis-annelated decahydroquinoline alkaloids can be synthesized stereoselectively. This methodology of asymmetric synthesis is based on the effect that both enantiomers of 2,6-disubstituted piperidin-4-ones are selectively and alternatively accessible using the auxiliary as the identical stereodifferentiating tool. In addition, the carbohydrate auxiliary controls the stereoselective protonation of enolates formed by conjugate addition of cuprates to N-galactosyl octahydroquinolin-4-ones. The syntheses of trans-4a-epi-pumiliotoxin C and cis-4a-epi-perhydro-219A illustrate this concept of asymmetric synthesis of decahydroquinoline alkaloids.

Auxiliary-controlled stereoselective enolate protonation: Enantioselective synthesis of cis and trans annulated decahydroquinoline alkaloids

The diastereoselective synthesis of the octahydroquinoline enone precursor of pumiliotoxin C is achieved via tandem Mannich-Michael reaction on N-galactosyl imines. Conjugate cuprate addition to the bicyclic enone stereoselectively forms the trans annulated 4a-epi-pumiliotoxin C skeleton in the presence of the carbohydrate auxiliary, and the cis annulated pumiliotoxin C skeleton in its absence.

A Short, Asymmetric Synthesis of (-)-Pumiliotoxin C

An asymmetric synthesis of (-)-pumiliotoxin C is accomplished in nine steps from 4-methoxy-3-(triisopropylsilyl)pyridine.