1. Group Meeting Zefan Hurley 6/9/17

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

3. 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

4. Reduction of Amides

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

6. Reduction of Tertiary Amides

7. Pop Mechanism

8. Chemoselective Reduction of Tertiary Amides with LAB Reagents

9. Reduction of Amides with Lithium Pyrrolidinoborohydride

10. Reduction of Lactams to Amines with Lithium Dimethylaminoborohydride

11. Reduction of Weinreb Amides to Aldehydes with MgAB

12. Reduction of Tertiary Amides to Aldehydes with MgAB

13. Pop Mechanism

14. 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.

15. 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

16. Retrosynthetic Analysis of (-)-Himandrine (1)

17. Enantioselective Synthesis of Tricyclic Enone (-)

18. Enantioselective Total Synthesis of (-)-Himandrine

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

20. Now Leave.