Publication | Closed Access
Asymmetric Synthesis of (-)-Tetrahydrolipstatin
55
Citations
0
References
1991
Year
Bioorganic ChemistryEngineeringBiochemistryIron Octanoyl ComplexNatural SciencesAsymmetric SynthesisOrganic ChemistryStereoselective SynthesisNatural Product Synthesisβ-Propiolactone FunctionalitySynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
The asymmetric synthesis of the β-propiolactone functionality of tetrahydrolipstatin was achieved via a stereoselective aldol reaction between the iron octanoyl complex (S)-[(η5-C5H5)Fe(CO)(PPh3)COC7H15] and (S)-3-benzyloxytetradecanal (obtained via a Noyori asymmetric hydrogenation of methyl 3-oxotetradecanoate) followed by oxidative decomplexation. Subsequent debenzylation and introduction of the N-formylleucine residue gave (-)-tetrahydrolipstatin.