Synthesis of the C22-C37 segment of prorocentin |
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Authors: | Atsushi TakemuraYasushi Katagiri Kenshu Fujiwara Hidetoshi Kawai Takanori Suzuki |
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Affiliation: | a Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan b PRESTO, Japan Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama 332-0012, Japan |
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Abstract: | The synthesis of the C22-C37 segment of prorocentin, isolated from the dinoflagellate Prorocentrum lima, was achieved. Because the relative stereochemical relationship between C26 and other stereocenters (C28/C31/C32 established as R*/R*/R*) in the C22-C37 region of natural prorocentin has not yet been determined, both epimers at C26 of the C22-C37 segment were selectively constructed. The synthesis was based on a 5-exo epoxide ring opening reaction to form an oxolane (E-ring), Brown asymmetric methallylation to install the C26-stereocenter, acryloylation of the resulting alcohol, and ring-closing olefin metathesis to establish the Z-olefin at C23/C24. |
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