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Total Synthesis of ( − )-Lepenine Yiyun Peng 5/6/2014 doi.org/10.1021/ja503023h |J. Am. Chem. Soc. XXXX, XXX, XXX − XXX Yoshitake Nishiyama, Yuki Han-ya,

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Presentation on theme: "Total Synthesis of ( − )-Lepenine Yiyun Peng 5/6/2014 doi.org/10.1021/ja503023h |J. Am. Chem. Soc. XXXX, XXX, XXX − XXX Yoshitake Nishiyama, Yuki Han-ya,"— Presentation transcript:

1 Total Synthesis of ( − )-Lepenine Yiyun Peng 5/6/2014 doi.org/ /ja503023h |J. Am. Chem. Soc. XXXX, XXX, XXX − XXX Yoshitake Nishiyama, Yuki Han-ya, Satoshi Yokoshima, and Tohru Fukuyama

2 Tohru Fukuyama’s Correction Crisis

3

4 Background

5 Retrosynthesis

6 Forward synthesis Mitsunobu Reaction

7 Forward synthesis Johnson-Claisen Rearrangement Claisen Rearrangement

8 Forward synthesis COOH Friedel-Crafts Reaction Mechanism? Without AlCl 3 Dehydration of tertiary alcohol Replaced pivaloyl group with a methacryloyl group radical scavenger Hydroboration occurred exclusively from the convex face

9 Forward synthesis Reductive amination Kagan's reagent How? Mannich Reaction Diels-Alder reaction

10 Forward synthesis Reductive amination ? Luche Reduction Selectively reduce α, β -unsaturated ketone


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