108552-80-3

Upstream product

• 58845-50-4 ((2R,3R)-3-methyloxiran-2-yl)methanol 
• 65-85-0 benzoic acid 
• 108552-79-0 (2R,3S)-1,2-O-cyclohexylidene-1,2,3-butanetriol 3-benzoate 
• 98-88-4 benzoyl chloride 

Downstream Products

• 108552-81-4 benzoic acid 1-methyl-2-oxo-ethyl ester 
• 1407163-76-1 (1S)-1-((4R)-2-phenyl-1,3-dioxolan-4-yl)ethyl benzoate 

Relevant academic research and scientific papers

Stereoselective total synthesis of dinemasone A by double intramolecular hetero-Michael addition (DIHMA)

The first total synthesis of dinemasone A, a bioactive metabolite with a spiroketal moiety, is described. The main strategy for the construction of the spiroketal unit involves a double intramolecular hetero-Michael addition (DIHMA) of an ynone moiety. The thus obtained axial-equatorial mono anomeric spiroketal, on spiroepimerization with ZnBr2, was converted into the requisite axial-axial double anomeric spiroketal. The ynone moiety with four stereocentres, was prepared from a chiral propargylic alcohol (C5-C11 fragment) and a dihydroxy aldehyde (C1-C4 fragment), which in turn were obtained from d-mannitol and crotyl alcohol respectively.

Synthese of Natural (-)-Osmundalactone and Its Epimer

(-)-Osmundalactone, an aglycone of osmundalin, and its 5-epimer were synthesized from 3-triethylsiloxy-1-propyne and from (S)-1-methyl-2-oxoethyl benzoate, which was derived from 2,3-O-cyclohexylidene-D-glyceraldehyde.