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

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 applic...

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Bibliographic Details
Published in:Organic letters 2003-04, Vol.5 (7), p.1123-1126
Main Authors: Yasuhara, Tomohisa, Nishimura, Katsumi, Yamashita, Mitsuaki, Fukuyama, Naoshi, Yamada, Ken-ichi, Muraoka, Osamu, Tomioka, Kiyoshi
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Amaryllidaceae Alkaloids
Cyclization
Esters - chemistry
Molecular Structure
Nitrogen - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0341905