21041-42-9

Basic information

• Product Name: luciduline
• Synonyms: luciduline;(3R,4aβ,8aβ)-1,7β-Dimethyl-3α,5α-ethanodecahydroquinoline-10-one;(3R,4aβ,8aβ)-Decahydro-1,7β-dimethyl-3,5α-ethanoquinolin-10-one
• CAS NO: 21041-42-9
• Molecular Formula: C13H21NO
• Molecular Weight: 207.31194
• Mol File: 21041-42-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 300.1°Cat760mmHg
• Flash Point: 126.5°C
• Appearance: /
• Density: 1.023g/cm³
• Vapor Pressure: 0.000794mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: luciduline(CAS DataBase Reference)
• NIST Chemistry Reference: luciduline(21041-42-9)
• EPA Substance Registry System: luciduline(21041-42-9)

Safety Data

• Hazardous Substances Data: 21041-42-9(Hazardous Substances Data)

Usage

Description

Luciduline is a unique type of Lycopodium alkaloid that has been obtained from L.lucidulum. It is present among the weak bases of the alkaloidal extract and has a complete structure, including the absolute configuration, which has been determined from chemical and physical evidence, together with an X-ray diffraction study of O-p-bromobenzoyldihydroluciduline.

Uses

Luciduline is used as a pharmaceutical compound for its potential therapeutic applications. It is derived from natural sources and has been studied for its chemical and physical properties, making it a promising candidate for various applications in the pharmaceutical industry.
Used in Pharmaceutical Industry:
Luciduline is used as a compound for research and development in the pharmaceutical industry. Its unique structure and properties make it a valuable asset for the discovery and development of new drugs and therapies.

References

Ayer, Masaki, Nkunika., Can. J. Che m., 46, 363 I (1968)

InChI:InChI=1/C13H21NO/c1-8-3-9-6-13(15)10-5-11(9)12(4-8)14(2)7-10/h8-12H,3-7H2,1-2H3/t8-,9+,10-,11-,12+/m1/s1

Upstream product

• 1310457-11-4 benzyl (3R,4aS,7S,8aS)-3-acetyl-7-methyl-5-oxooctahydroquinoline-1(2H)-carboxylate 
• 1310457-15-8 benzyl (3S,4aS,7S,8aS)-3-ethenyl-7-methyl-5-oxooctahydroquinoline-1(2H)-carboxylate 
• 1310457-12-5 benzyl (3S,4aS,8aS)-3-ethenyl-5-oxo-3,4,4a,5,6,8a-hexahydroquinoline-1(2H)-carboxylate 
• 50-00-0 formaldehyd 
• 1310457-10-3 benzyl (1S,3R,7R,8aR)-3-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-1,7-(epiminomethano)naphthalene-10-carboxylate 
• 1042150-18-4 (R)-methyl 3-(4-methyl-6-oxocyclohex-1-enyl)propanoate 
• 240129-01-5 (+)-(S)-1-[(benzyloxy)carbonyl]-2-[(R)-5-(methoxycarbonyl)-2-methyl-4-pentenyl]-2,3-dihydro-4-pyridone 
• 240129-06-0 (-)-(S)-1-[(benzyloxy)carbonyl]-2-[(S)-2-methyl-4-oxobutyl]-2,3-dihydro-4-pyridone 
• 240128-95-4 (-)-(S)-1-[(benzyloxy)carbonyl]-2-[(R)-2-methyl-4-pentenyl]-2,3-dihydro-4-pyridone 
• 240129-00-4 (-)-(S)-2-[(R)-2-methyl-4-pentenyl]-2,3-dihydro-4-pyridone 
• 240128-99-8 (+)-(S)-[(R)-2-methyl-4-pentenyl]-1-[(1S,2R)-2-((1-methyl-1-phenyl)ethyl) cyclohexyl-oxycarbonyl]-5-(triisopropylsilyl)-2,3-dihydro-1H-pyridine-4-one 

Relevant articles and documents

Concise total syntheses of the lycopodium alkaloids (±)-nankakurines A and B via luciduline

(Figure presented) Total syntheses of the Lycopodium alkaloids nankakurines A and B have been accomplished In 6 and 7 steps, respectively, via a sequence that passes through a third Lycopodium alkaloid, luciduline, and forgoes the use of protecting groups on nitrogen. Key features include a short preparation of luclduline followed by a concise and stereoselective amlnoallylatlon/ring-closlng metathesis protocol to fashion the spiropiperidine ring common to nankakurines A and B.

Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (-)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline

The synthesis of the Lycopodium alkaloids, (-)-cermizine B, (+)-serratezomine E, and (+)-luciduline using phenylglycinol-derived tricyclic lactams as chiral scaffolds, is reported. The requisite lactams are prepared by a cyclocondensation reaction between (R)- or (S)-phenylglycinol and the substituted δ-keto ester 11, easily accessible from (R)-pulegone. The factors governing the stereoselectivity of these cyclocondensation reactions are discussed. Key steps of the synthesis from the stereochemical standpoint are the stereoselective elaboration of the allyl substituent to the (S)-2-(piperidyl)methyl moiety and the stereoselective removal of the chiral inductor to give a cis-decahydroquinoline.

IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: Asymmetric synthesis of (+)-luciduline

(equation presented) The first chiral auxiliary mediated asymmetric synthesis of the naturally occurring Lycopodium alkaloid (+)-luciduline has been accomplished. Key steps include an IMDA reaction of a chiral dihydropyridine, a subsequent retro-Mannich r