CI H3CO H3CO OCH, 1. NaH, THF CN КОН/Н,О 2. MEOCH,CI, THF DMSO (A) (В) (C) ČN (D) COOH H3CO ARCO,H 1. КОН/Н,О L/KI, NaHCO, NaHCO,,CH,CI, 2. CO, OMe H,O OMe НО (F) НО (G) (E) Ac,O Pyridine BugSnH BBr, CrO, Pyridine OMe OMe ОН СНО AcO (H) AcO (I) AcO (J) AcO (К) (Corey lactone)
Carbohydrates
Carbohydrates are the organic compounds that are obtained in foods and living matters in the shape of sugars, cellulose, and starch. The general formula of carbohydrates is Cn(H2O)2. The ratio of H and O present in carbohydrates is identical to water.
Starch
Starch is a polysaccharide carbohydrate that belongs to the category of polysaccharide carbohydrates.
Mutarotation
The rotation of a particular structure of the chiral compound because of the epimerization is called mutarotation. It is the repercussion of the ring chain tautomerism. In terms of glucose, this can be defined as the modification in the equilibrium of the α- and β- glucose anomers upon its dissolution in the solvent water. This process is usually seen in the chemistry of carbohydrates.
L Sugar
A chemical compound that is represented with a molecular formula C6H12O6 is called L-(-) sugar. At the carbon’s 5th position, the hydroxyl group is placed to the compound’s left and therefore the sugar is represented as L(-)-sugar. It is capable of rotating the polarized light’s plane in the direction anticlockwise. L isomers are one of the 2 isomers formed by the configurational stereochemistry of the carbohydrates.
Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined.
Q. What is the function of the carbon dioxide added to the reaction mixture in Step 2 of the conversion of (E) to (F)? Hint: What happens when carbon dioxide is dissolved in water? Why not just use HCl?
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