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Total Synthesis of (−)- Lepenine

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.

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Total Synthesis of (−)- Lepenine

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  1. Total Synthesis of (−)-Lepenine YiyunPeng 5/6/2014 doi.org/10.1021/ja503023h |J. Am. Chem. Soc. XXXX, XXX, XXX−XXX YoshitakeNishiyama, 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 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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