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):(a) Identify the most acidic proton in  1 and justify your choice using any necessary drawings.

🤓 Based on our data, we think this question is relevant for Professor Staff's class at UBC.

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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):

(a) Identify the most acidic proton in  1 and justify your choice using any necessary drawings.

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Our tutors have indicated that to solve this problem you will need to apply the pKa concept. You can view video lessons to learn pKa. Or if you need more pKa practice, you can also practice pKa practice problems.

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Based on our data, we think this problem is relevant for Professor Staff's class at UBC.

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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.