Pure Appl. Chem., 2005, Vol. 77, No. 7, pp. 1131-1137
http://dx.doi.org/10.1351/pac200577071131
Total synthesis of zincophorin
Abstract:
A total synthesis of the naturally occurring ionophore zincophorin has been realized. The key steps are an intramolecular oxymercuration of a cyclopropanemethanol for the elaboration of the tetrahydropyran ring and a Carroll–Claisen rearrangement to control the configuration of the double bond at C20–C21 as well as the stereogenic center at C21.
Keywords
Carroll-Claisen rearrangement; griseocholin; ionophore; oxymercuration; Streptomyces griseus; zincophorin.