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Total Synthesis of (±)-α- and β-Lycoranes by Sequential Chemoselective Conjugate Addition−Stereoselective Nitro-Michael Cyclization of an ω-Nitro-α,β,ψ,ω-unsaturated Ester

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journal contribution
posted on 26.02.2003, 00:00 by Tomohisa Yasuhara, Katsumi Nishimura, Mitsuaki Yamashita, Naoshi Fukuyama, Ken-ichi Yamada, Osamu Muraoka, Kiyoshi Tomioka
An ω-nitro-α,β,ψ,ω-unsaturated ester underwent a chemoselective conjugate addition of a nitroolefin moiety with aryllithium to produce a ψ-aryl-ω-nitro-α,β-unsaturated ester, which was then stereoselectively cyclized by intramolecular nitro-Michael reaction giving a functionalized cyclohexane applicable to the total synthesis of (±)-α- and β-lycoranes.

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