7688-58-6

Usage

Uses

Unfortunately, the provided materials do not specify any particular applications or uses for (3S)-2,3,4,10-Tetrahydro-3-hydroxy-2,2,10-trimethyl-5H-pyrano[2,3-b]quinolin-5-one. However, given that it is a pyranoquinolone alkaloid, it may have potential applications in various fields such as pharmaceuticals, agrochemicals, or as a natural product with biological activity, similar to other alkaloids. Further research and development would be required to explore and confirm its specific uses.

References

Corral, Orazi., Tetrahedron Lett., S83 (1967) Synthesis: Bowman, Grundon., 1. Chem. Soc., C, IS04 (1966)

InChI:InChI=1/C15H17NO3/c1-15(2)12(17)8-10-13(18)9-6-4-5-7-11(9)16(3)14(10)19-15/h4-7,12,17H,8H2,1-3H3

Upstream product

• 88148-17-8 3-bromo-10-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-oxa-9-aza-anthracene 
• 155102-07-1 (+)-(3R,4S)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-3,4-dihydro-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline 
• 155102-08-2 (-)-(3S,4S)-3,4-dihydro-3,4-epoxy-5-methoxy-2,2-dimethyl-2H-pyrano[2,3-b]quinoline 
• 88148-18-9 5-methoxy-2,2-dimethyl-(2H)-pyrano<2,3-b>quinoline 
• 7282-19-1 atanine 
• 72855-84-6 (+)-(3S)-geibalansine 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Synthesis and absolute stereochemistry assignment of enantiopure dihydrofuro- and dihydropyrano-quinoline alkaloids

The chiral quinoline alkaloids platydesmine 3, platydesmine methosalt 4 and edulinine 9, have been synthesised in enantiopure form via asymmetric dihydroxylation of the achiral alkaloid atanine 1. Chromatographic separation of MTPA diastereoisomers 20 formed from racemic bromohydrin derivatives of atanine 1 was a key step in the synthesis of geibalansine 7, edulinine 9, ribalinine 10, Ψ-ribalinine 11 and araliopsine 12 as single enantiomers. The absolute configurations of (+)-platydesmine methosalt 4 and (-)-Ψ-ribalinine 11 were unequivocally determined by X-ray crystallography while stereochemical correlation and circular dichroism spectroscopy methods were used to assign absolute configurations to platydesmine 3, geibalansine 7, ribalinine 10, araliopsine 12 and edulinine 9. Possible errors which earlier led to the incorrect assignment of absolute configurations of the quinoline alkaloids platydesmine 3, platydesmine methosalt 4, edulinine 9, araliopsine 12 and other related chiral quinoline alkaloids are discussed.

A general synthetic route to enantiopure quinoline alkaloids

Enantiopure chromenoquinoline epoxides of established configuration are obtained by cyclization of their resolved bromomethoxy(trifluoromethyl)phenylacetates and provide a new route to geibalansine, O-acetylgeibalansine, ribalinine, araliopsine, edulinine and related quinoline alkaloids.