Phenalamide A2 belongs to a class of natural products that are of interest because of

Chapter 1, Problem 1.73

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Phenalamide A2 belongs to a class of natural products that are of interest because of their antibiotic, antifungal, and antiviral activity. In the first total synthesis of this compound, the following boronate ester was utilized (Org. Lett. 1999, 1, 17131715): O C O C C C C C B C O C C O H3C CH3 CH3 CH3 H H H H H H H H H (a) Determine the hybridization state of the boron atom. (b) Predict the O!B!O bond angle and then suggest a reason why the actual bond angle might deviate from the predicted value in this case. (c) The lone pairs have not been drawn. Draw all of them. (Hint: Note that the structure has no formal charges.)

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