Synthetic studies towards (+)-symbioimine

ORGN 748

Stephen Born, Erin E. Olson, and Yoshihisa Kobayashi, ykoba@chem.ucsd.edu. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Dr #0343, La Jolla, CA 92093-0343
Symbioimine 1, isolated by Uemura in 2004 from a cultured symbiotic marine dinoflagellate Symbiodinium sp., has received considerable attention as a potential target for the treatment of osteoporosis by inhibiting the differentiation of RAW264 cells into osteoclasts. These biological properties coupled with its unusual tricyclic iminium architecture has prompted interest from several synthetic groups in its biosynthesis via an intramolecular Diels-Alder (IMDA) reaction. Herein, we present our current efforts based on a flexible, convergent strategy enabling access to the advanced intermediate 3.