1. Mohammad Movassaghi,* Meiliana Tjandra, and Jun Qi Reporter: ZhiYong Han 2009-07-06 Total Synthesis of (-)-Himandrine J. AM. CHEM. SOC ASAP

2. Hzy-090706 2 Author Mohammad Movassaghi Associate Professor of Chemistry Massachusetts Institute of Technology B.S. University of California at Berkeley 1995 Ph.D. Harvard University 2001

3. Hzy-090706 3 Origin Galbulimima belgraveana Cannabis( 大麻 ) Similarity Hallucinogen( 迷幻剂 ) Popuans( 巴布亚人 ) Sleeping Popuan Boil

4. Hzy-090706 4 Structure

5. Hzy-090706 5 Retro synthesis

6. Hzy-090706 6

7. 7 Tetrakis(triphenylphosphine)palladium (1.54 g, 1.30 mmol, 8.00 mol%) and thallium carbonate (15.7 g, 33.0 mmol, 2.00 equiv) were added sequentially

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14. Hzy-090706 14 Macmillan α-Oxidation of Aldehydes MacMillan, D. W. C. J. Am.Chem. Soc. 2003, 125, 10808.

15. Hzy-090706 15 Buchwald’s copper promoted coupling Buchwald, S. L. Org. Lett. 2003, 5,3667.

16. Hzy-090706 16 Martin’s sulfurane dehydrating reagent Martin, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 2339, 2341. Dehydrates secondary and tertiary alcohols to give olefins, but forms ethers with primary alcohols. Example 1: Example 2:

17. Hzy-090706 17 Vilsmeier–Haack reaction

18. Hzy-090706 18