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Total Synthesis of (+)-Biotin

Total Synthesis of (+)-Biotin. Hoffmann-La Roche J. Am. Chem. Soc. 1982 , 104 , 6460-6462. Presented by Derek Ahneman. Hoffmann-La Roche, Inc. Swiss global health care company Founded by Fritz Hoffmann-La Roche in 1896 Headquartered in Basel, Switzerland

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Total Synthesis of (+)-Biotin

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  1. Total Synthesis of (+)-Biotin Hoffmann-La Roche J. Am. Chem. Soc.1982, 104, 6460-6462. Presented by Derek Ahneman

  2. Hoffmann-La Roche, Inc. • Swiss global health care company • Founded by Fritz Hoffmann-La Roche in 1896 • Headquartered in Basel, Switzerland • EnricoBaggiolini’s group located in Nutley, NJ • Roche in FY 2011: • Revenue: $47 billion • Profit: $10 billion • Over 80,000 employees

  3. Biotin • Essential water soluble vitamin (B7) • Coenzyme in the synthesis of fatty acids, isoleucine, and valine • Also plays a role in gluconeogenesis, or generation of glucose from non-carbohydrate sources (lactate, etc.) • Produced by intestinal bacteria • Tetrahydrothiophene ring with cyclic urea • Three contiguous stereocenters

  4. Retrosynthetic Analysis of Biotin

  5. Synthesis of (+)-Biotin

  6. Synthesis of (+)-Biotin

  7. Conclusion • Total synthesis of (+)-biotin is reported • Relatively simple and inexpensive starting materials • Key step is an intramolecularnitrone-olefin [3+2] cycloaddition reaction • Diastereoselectivity controlled by conformation of ten-membered ring …Questions?

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