Progress toward the total synthesis of massadine

ORGN 746

Gary M. Chinigo, chinigo@org.chem.ethz.ch1, Alexander Breder1, Andrew W. Waltman1, and Erick M. Carreira, carreira@org.chem.ethz.ch2. (1) Laboratorium fur Organische Chemie, ETH Zurich, HCI H338, Wolfgang-Pauli-Strasse 10, Zurich, 8046, Switzerland, (2) Laboratory of Organic Chemistry, ETH Zurich, Swiss Federal Institute of Technology, Wolfgang-Pauli-Strasse 10, Zurich, 8093, Switzerland
Described herein is our progress toward the asymmetric synthesis of the marine natural product massadine. The strategy includes: application of a cationic norbornyl rearrangement, ozonolytic cleavage displaying remarkable end-group differentiation, and a Barton decarboxylation-oxygenation for the installation of the hindered secondary alcohol found in massadine.