Ch. 12 - Alcohols, Ethers, Epoxides and ThiolsWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Solution: 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 anti

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.