A straightforward synthesis of (-)-phaseolinic acid.
A concise approach to (-)-phaseolinic acid starting from commercially available (S)-oct-1-yn-3-ol is disclosed. The key steps are a ring-closing metathesis reaction to prepare a C(2)-symmetrical allylic diol and its desymmetrization to a gamma-butyrolactone by using an Ireland-Claisen rearrangement. The 2S,3S,4S configuration of the levogyre natural product has been confirmed.
Amador
Marta
M
Departament de Química Orgànica, Universitat de Barcelona, C/ Martí i Franquès 1-11, E-08028 Barcelona, Catalonia, Spain.
Ariza
Xavier
X
Garcia
Jordi
J
Ortiz
Jordi
J
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D001487:Basidiomycota / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism
D001685:Biological Factors; D007202:Indicators and Reagents; C494217:phaseolinic acid; D015107:4-Butyrolactone