60300-67-6

Upstream product

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 100-52-7 benzaldehyde 

Downstream Products

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 129594-73-6 (1R,3R,4R)-3-((S)-Hydroxy-phenyl-methyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 100-52-7 benzaldehyde 
• 180182-51-8 (1R,2R,3S,4R)-3-((R)-Hydroxy-phenyl-methyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol 
• 134305-00-3 (1S,3R,4S)-3-((S)-Hydroxy-phenyl-methyl)-1,7,7-trimethyl-bicyclo[2.2.1]hept-5-en-2-one 
• 134304-99-7 (1S,3S,4S)-3-((R)-Hydroxy-phenyl-methyl)-1,7,7-trimethyl-bicyclo[2.2.1]hept-5-en-2-one 
• 129594-74-7 (1R,3S,4R)-3-((S)-1-Hydroxy-2-phenyl-ethyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 83195-80-6 (1R,3S,4S)-3-((R)-Hydroxy-phenyl-methyl)-bicyclo[2.2.1]heptan-2-one 
• 129594-75-8 (1R,3R,4R)-3-((R)-1-Hydroxy-2-phenyl-ethyl)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 

Relevant academic research and scientific papers

Synthesis and Absolute Configuration of the Antiparasitic Furanosesquiterpenes (-)-Furodysin and (-)-Furodysinin. Camphor as a Six-Membered Ring Chiral Pool Template

The syntheses of (-)-furodysin ((-2)-2a) and (-)-furodysinin ((-)-3a) in four steps starting from (+)-9-bromocamphor (18) has been accomplished, thus establishing the absolute configuration of these and related metabolites.This was made possible by the unexpected exo selectivity in the aldol condensation of camphor-like enolates with aldehydes.This has been found to be a general phenomenon in the camphor system.Further, anionic fragmentation of the C1-C7 bond of camphor derivatives has allowed access to synthetic intermediates containing functionalized six-memberedrings, thus opening up avenues from camphor to a new class of chiral pool elements not currently available from chiral pool substances.

New camphor derivatives for enantioselective syntheses

New 1,3 diols 3a→3c were efficiently prepared in the enantiopure form in 50-68% yield (2 steps), from the available 1-(R)-(+)-camphor 1.

Stereoselectivity of C(3) methylation and aldol condensation of camphor and derivatives

The stereoselectivity of methylation and aldol condensation of camphor and derivatives is determined by the presence or absence of a C(7) syn-methyl group and (or) C(5) and C(6) endo-hydrogen atoms.

Synthesis and Absolute Configuration of (-)-Furodysinin. New Transformations of Camphor Derivatives

The synthesis of (-)-furodysinin ((-)-3a) has been accomplished in five steps from (+)-?--bromocamphor (7) and has allowed assignment of the absolute configuration of a number of marine furanosesquiterpenes produced by sponges of the genus Dysidea.