The Stille reaction in the synthesis of the C37-norcarotenoid butenolide pyrrhoxanthin. Scope and limitations |
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Authors: | Vaz Belén Domínguez Marta Alvarez Rosana de Lera Angel R |
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Institution: | Departamento de Química Organica, Facultade de Química, Universidade de Vigo, Lagoas Marcosende, E-36310, Vigo, Spain. |
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Abstract: | The sequential Stille cross-coupling reactions of the dihalogenated gamma-alkylidenebutenolide 7 with stannanes 9 and 6 afforded the carbon skeleton of pyrrhoxanthin, a highly functionalized C7'-C8' acetylenic C37-norcarotenoid butenolide. Although the first halogen-selective Stille coupling takes place in 90% yield at ambient temperature, double isomerization of the Z,E- to the E,Z-C7'-C10' enyne, likely induced by the catalyst, accompanyied the bond formation, leading to 9'Z-20 and, ultimately, to 9'Z-pyrrhoxanthin 9'Z-1. |
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