Corey aldehyde benzoate

Lithium chloride (2.6 g) is dissolved in THF (170 mL). Dimethyl-(2-oxo-4-phenylbutyl)phosphonate (7.87 g) and triethylamine (4.3 mL) are added. The mixture is stirred and cooled to -10°C. A solution of the Corey aldehyde benzoate, (lS,5R,6R,7R)-6-formyl-7-(benzyloxy)-2-oxabicyclo[3.3.0]octan-3-one (8.42 g) in THF (75 mL) is added to the reaction mixture over three hours. The resulting mixture is stirred for 18 hours at -10°C. At the end of this time, methyl t-butyl ether (MTBE) (100 mL) is added and the mixture warmed to 0-20°C. Sodium bisulfite (38%, 100 mL) is added and the two-phase mixture was stirred for 10 min. The phases are separated and the organic phase is washed with saturated aqueous sodium bicarbonate solution (100 mL). The organic phase is separated and concentrated under reduced pressure to a volume of <100 mL. Ethyl acetate (200 mL) is added and the... 

The Pfizer process to latanoprost starts with the Corey aldehyde benzoate (13, CAB), available as a relatively stable crystalline solid via the historic Upjohn prostaglandin synthesis (Scheme 3).17 The reaction of the phosphonate with CAB (13) is done using... 

In the synthesis of LTB4-like compounds, Corey s group used the aldehyde benzoate (S)-68a in syntheses of LTB4 (Schemes 3.10 and 3.11), LTB (Scheme 3.16), and (6 )-LTB4 (not shown). 

D-Glucose ([52], Fig. 9) has served as an intriguing educt for preparation (31) of the Corey lactone equivalent [59] (32). The iodo compound [53] was readily available from glucose in four steps. Reductive fragmentation, induced by zinc in ethanol, gave the unsaturated aldehyde [54]. Reaction with N-methylhydroxylamine was followed by a spontaneous nitrone cycloaddition to provide the oxazolidine [55]. Catalytic reduction of the N-O bond was accompanied by the unexpected loss of tosylate and aziridine formation. Olefin formation from [56] via the N-oxide and chain extension gave acid [57]. lodolactonization and tri-n-butyltin hydride reduction in the standard fashion led to lactone [58]. After saponification of the benzoates, stereoselective epoxide formation gave epoxy lactone [59]. 

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