During a total synthesis of 2-methyl-d-erythritol (a sugar of importance to isoprenoid
Chapter 14, Problem 14.71(choose chapter or problem)
During a total synthesis of 2-methyl-d-erythritol (a sugar of importance to isoprenoid biosynthesis), epoxide 2 was required (J. Org. Chem. 2002, 67, 48564859). (a) Identify the reagents you would use to achieve a stereoselective synthesis of epoxide 2 from allylic alcohol 1. (b) Propose a plausible mechanism for the formation of orthoester 4 from epoxide 3 upon treatment with a catalytic amount of aqueous acid. (Hint: The O in the CRO bond of the ester group can function as a nucleophilic center.) OH Ph O O OH H O Ph O H O Ph O O [H3O+] O O Ph O O 1 2 4
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