Total Synthesis of (−)-Lepenine

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Presentation transcript:

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, Satoshi Yokoshima, and Tohru Fukuyama

Tohru Fukuyama’s Correction Crisis

Tohru Fukuyama’s Correction Crisis

Background

Retrosynthesis

Forward synthesis Mitsunobu Reaction

Forward synthesis Johnson-Claisen Rearrangement Claisen Rearrangement

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

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

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