Total synthesis of zincophorin*
Janine Cossy, Christophe Meyer, Magali Defosseux, and Nicolas Blanchard
Laboratoire de Chimie Organique, Associé au CNRS, ESPCI, 10 rue Vauquelin 75231 Paris Cedex 05, France
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: ionophore; zincophorin; oxymercuration; Carroll–Claisen rearrangement; griseocholin; Streptomyces griseus.
*An issue of reviews and research papers based on lectures presented at the 15th International Conference on Organic Synthesis (ICOS-15), held in Nagoya, Japan, 1-6 August 2004, on the theme of organic synthesis. Other presentations are published in this issue, pp. 1087-1296.