American Chemical Society
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Biomimetic Asymmetric Total Synthesis of (−)-Laurefucin via an Organoselenium-Mediated Intramolecular Hydroxyetherification

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posted on 2008-12-10, 00:00 authored by Byungsook Kim, Miseon Lee, Mi Jung Kim, Hyunjoo Lee, Sanghee Kim, Deukjoon Kim, Minseob Koh, Seung Bum Park, Kye Jung Shin
The first asymmetric total synthesis of (−)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.