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

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

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

Hzy Structure

Hzy Retro synthesis

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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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9

10

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

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

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

Hzy Vilsmeier–Haack reaction

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