Problem: Briarellin E, compound 3, is produced by coral in the Carribean and Mediterranean seas and belongs to a larger family of marine natural products that are currently being investigated as potential anticancer agents. During a recent synthesis of Briarellin E, compound 1 was treated with TBAF (tetrabutylammonium fluoride) to give compound 2 (J. Org. Chem., 2009, 74, 5458-5470). Draw the structure of compound 2 using the shown structure of compound 1 including wedges and dashes indicating the stereochemistry.

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Briarellin E, compound 3, is produced by coral in the Carribean and Mediterranean seas and belongs to a larger family of marine natural products that are currently being investigated as potential anticancer agents. During a recent synthesis of Briarellin E, compound 1 was treated with TBAF (tetrabutylammonium fluoride) to give compound 2 (J. Org. Chem., 2009, 74, 5458-5470). Draw the structure of compound 2 using the shown structure of compound 1 including wedges and dashes indicating the stereochemistry.

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Based on our data, we think this problem is relevant for Professor Osborn's class at Southwest Tennessee Community College.