Transcript Total Synthesis of (−)

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
Friedel-Crafts Reaction
Mechanism? Without AlCl3
Replaced pivaloyl group
with a methacryloyl group
Hydroboration occurred
exclusively from the convex face
Dehydration of tertiary alcohol
radical scavenger
Forward synthesis
Reductive amination
Mannich Reaction
Diels-Alder reaction
Kagan's reagent
How?
Forward synthesis
Reductive amination
Luche Reduction
Selectively reduce α, β-unsaturated ketone
?