228548-03-6

Upstream product

• 228547-90-8 (3aR,8aS)-2,2-Dimethyl-5-oxo-hexahydro-cyclohepta[1,3]dioxole-6-carboxylic acid benzyl ester 
• 228547-88-4 (4R,5S)-2-oxo-4,5-O-isopropylidene-cycloheptane-1-carboxylic acid ethyl ester 
• 228547-92-0 (3R,4S)-3,4-O-isopropylidene-cycloheptan-1-one 
• 121573-17-9 (3aR,7aS)-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

From (-)-quinic acid to 8-azabicyclo[3.2.1]octane framework: Preparation of an enantiopure tropan-6α-ol

The carbon atom ring-insertion via pyrolysis of an α-diazo-β-hydroxy ester intermediate, in turn obtained by reaction between ethyldiazoacetate and 3,4-O-isopropylidene-3(R),4(S)-dihydroxycyclohexanone 2, a chiron easily prepared through a five step sequence from D(-)-quinic acid 1, was the key step for the construction of the cycloheptanone derivative 8. Its transformation into azidosulfate 18 set the stage for the preparation of the N-protected 8-azabicyclo[3.2.1]octane derivative 22, which, to the best of our knowledge, has been never obtained in optically pure form, as well as the tropan-6α-ol 24, obtained by reduction with LiAlH4.