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Towards the Total Synthesis of Manzamines: Preparation and Reactions of 2-Methoxycarbonyl-1,3-butadienes and β-Amino Aldehydes<sup>1,2</sup>
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1992
Year
ß-Amino Aldehydes 13Diversity Oriented SynthesisEngineeringHeterocyclicBiochemistryNatural SciencesDiversity-oriented SynthesisTotal SynthesisOrganic ChemistryN-disubstituted 1-Aminoethyl-2-methoxycarbonyl-1,3-butadienes 12ChemistryHeterocycle ChemistryNatural Product SynthesisVersatile SynthesesSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
The rapid and versatile syntheses of N,N-disubstituted 1-aminoethyl-2-methoxycarbonyl-1,3-butadienes 12 via ß-amino aldehydes 13, and 2-methoxycarbonyl-1-propyl-1,3-butadiene (7) are reported. The reactivity , of these dienes in the Diels-Alder reaction to form nitrogen heterocycles 8-10, 15 and 16, and their potential use in the synthesis of manzamines is discussed.