Total Synthesis and Structure Confirmation of (E) and (Z)-Ocellenyne Article Swipe

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Chemistry Absolute configuration Biogenesis Stereochemistry Single crystal Crystal structure Crystallography Gene Biochemistry

Harry B. Hicks , D. S. Brown , Hau Sun Sam Chan , Bruno A. Sousa , Kirsten E. Christensen , Jonathan W. Burton ·

YOU? · · 2022 · Open Access · · DOI: https://doi.org/10.1021/acs.orglett.2c03524 · OA: W4311222716

The (E/Z)-ocellenynes are C15 dibrominated Laurencia natural products whose structures have been subject to several reassignments on the basis of extensive NMR analysis, biosynthetic postulates, and DFT calculations. Herein, we report the synthesis of both (E)- and (Z)-ocellenyne, which, in combination with single crystal X-ray diffraction studies, allows their absolute configuration to be established and defines the configuration of the syn-12,13-dibromide as being (S, S) in keeping with their proposed biogenesis from the (6S, 7S)-laurediols.