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Total Synthesis of (−)-Lepenine

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Presentation on theme: "Total Synthesis of (−)-Lepenine"— 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 Tohru Fukuyama’s Correction Crisis

4 Background

5 Retrosynthesis

6 Forward synthesis Mitsunobu Reaction

7 Forward synthesis Johnson-Claisen Rearrangement Claisen Rearrangement

8 Forward synthesis COOH Dehydration of tertiary alcohol
Friedel-Crafts Reaction Mechanism? Without AlCl3 radical scavenger Replaced pivaloyl group with a methacryloyl group Hydroboration occurred exclusively from the convex face

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

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

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