total synthesis of 6-deoxyerethronolide b chem 635 kelsey roberts 05/07/13 gao, x.; woo, s.k.;...
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Total synthesis of 6-Deoxyerethronolide B
CHEM 635Kelsey Roberts
05/07/13
Gao, X.; Woo, S.K.; Krische M.J. J. Am. Chem. Soc. 2013, 135, 4223
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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.”
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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
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Retrosynthesis
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A B
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Synthesis of Portion A
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(S)-SEGPHOSChiral acid
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Synthesis of Portion A Continued
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Synthesis of Portion B
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Combining Both Sides
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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
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