Total synthesis of 6-Deoxyerethronolide B CHEM 635 Kelsey Roberts 05/07/13 Gao, X.; Woo, S.K.; Krische M.J. J. Am. Chem. Soc. 2013, 135, 4223.

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Presentation transcript:

Total synthesis of 6-Deoxyerethronolide B CHEM 635 Kelsey Roberts 05/07/13 Gao, X.; Woo, S.K.; Krische M.J. J. Am. Chem. Soc. 2013, 135, 4223

Michael J. Krische BS in Chemistry University of California Berkley PhD Stanford University under Dr. Barry M. Trost NIH Post Doc Dr. Jean- Marie Lehn Assistant Professor at University of Texas Austin 2004-Present- Full Professor Multiple Awards Publications Research focuses on: “catalytic reaction development with attendant applications in natural product synthesis.” 1

6-Deoxyerythronolide B 14 Membered Macrolide Other reported syntheses over 20 Longest linear steps Biogenic precursor to Erythromycin A and B, Erythronolide A and B, and (9S)-Dihydroerythronolide A 2

Retrosynthesis 3 AB

Synthesis of Portion A 4 (S)-SEGPHOS Chiral acid

Synthesis of Portion A Continued 5

Synthesis of Portion B 6

Combining Both Sides 7

Conclusion 14 Longest Linear Steps 20 Total Steps First use of two methods for alcohol CH-crotylation via transfer hydrogenation in total synthesis. Most concise construction of any erythronolide previously reported 8