Group Meeting Zefan Hurley 6/9/17

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Presentation transcript:

Group Meeting Zefan Hurley 6/9/17

Presentation Overview Controlled Reduction of Tertiary Amides to the Corresponding Alcohols, Aldehydes, or Amines Using Dialkylboranes and Aminoborohydride Reagents Total Synthesis of (-)-Himandrine

Controlled Reduction of Tertiary Amides to the Corresponding Alcohols, Aldehydes, or Amines Using Dialkylboranes and Aminoborohydride Reagents Christopher L. Bailey, Alexander Y. Joh, Zefan Q. Hurley, Christopher L. Anderson, and Bakthan Singaram* Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High Street, Santa Cruz, California 95064, United States J. Org. Chem. 2016, 81, 3619−3628

Reduction of Amides

Mechanism of the reduction of tertiary Mechanism of the reduction of tertiary amides with lithium aminoborohydrides.

Reduction of Tertiary Amides

Pop Mechanism

Chemoselective Reduction of Tertiary Amides with LAB Reagents

Reduction of Amides with Lithium Pyrrolidinoborohydride

Reduction of Lactams to Amines with Lithium Dimethylaminoborohydride

Reduction of Weinreb Amides to Aldehydes with MgAB

Reduction of Tertiary Amides to Aldehydes with MgAB

Pop Mechanism

Conclusion -Controlled room temperature reduction of various amides to either aldehydes or amines is presented. -Reduction product dependent on steric bulk around borane reducing agent. -Reagents easy to make and use.

Total Synthesis of (-)-Himandrine Mohammad Movassaghi,* Meiliana Tjandra, and Jun Qi Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139 JACS 2009, 131, 9648–9650

Retrosynthetic Analysis of (-)-Himandrine (1)

Enantioselective Synthesis of Tricyclic Enone (-)

Enantioselective Total Synthesis of (-)-Himandrine

Conclusions Fist total synthesis of (-)-himandrine 0.8% Yield over 20 linear steps

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