Problem: Asteltoxin, isolated from the cultures of Aspergillus stellatus, exhibits a potent inhibitory effect on the activity of E. coli BF1-ATPase. During S. L. Schreiber’s synthesis of asteltoxin, compound 1 was treated with a strong base to form anion 2 (J. Am. Chem. Soc. 1984, 106, 4186–4188):(b) Determine whether each of the following bases would be suitable for deprotonating compound 1 and explain your decision in each case: (i) NaOH, (ii) NaNH2, or (iii) CH3CO2Na.

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Asteltoxin, isolated from the cultures of Aspergillus stellatus, exhibits a potent inhibitory effect on the activity of E. coli BF1-ATPase. During S. L. Schreiber’s synthesis of asteltoxin, compound 1 was treated with a strong base to form anion 2 (J. Am. Chem. Soc. 1984, 106, 4186–4188):

(b) Determine whether each of the following bases would be suitable for deprotonating compound 1 and explain your decision in each case: (i) NaOH, (ii) NaNH2, or (iii) CH3CO2Na.

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 2nd Edition. You can also practice Organic Chemistry - Klein 2nd Edition practice problems.