1. 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

2. Michael J. Krische 1989- BS in Chemistry University of California Berkley 1996- PhD Stanford University under Dr. Barry M. Trost 1997-1999- NIH Post Doc Dr. Jean- Marie Lehn 1999-2003- Assistant Professor at University of Texas Austin 2004-Present- Full Professor Multiple Awards 175 + Publications Research focuses on: “catalytic reaction development with attendant applications in natural product synthesis.” 1

3. 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

4. Retrosynthesis 3 AB

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

6. Synthesis of Portion A Continued 5

7. Synthesis of Portion B 6

8. Combining Both Sides 7

9. 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