Pure Appl. Chem., 2005, Vol. 77, No. 7, pp. 1131-1137
doi:10.1351/pac200577071131
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: Carroll-Claisen rearrangement; griseocholin; ionophore; oxymercuration; Streptomyces griseus; zincophorin.
*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.
All articles from the 15th International Conference on Organic Synthesis (ICOS-15), Nagoya, Japan, 1–6 August 2004.