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Total Synthesis of Solandelactone I

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journal contribution
posted on 25.11.2015, 00:00 authored by Nils C. Eichenauer, Roxanne Tschersich, Jörg Pietruszka
Since the marine natural products solandelactones A–I were isolated from the hydroid Solanderia secunda and investigated by Seo et al. in 1996, considerable synthetic efforts toward these marine oxylipins followed. However, the structure elucidation of solandelactone I remained incomplete, and no synthesis has been reported. On the basis of our retrosynthetic analysis, the key building blocks were combined in a Horner–Wadsworth–Emmons reaction to create two common intermediates for the stereodivergent synthesis of all four diastereomers 14 matching the proposed structure of solandelactone I. Comparison of the published analytical data of natural product solandelactone I and data obtained from the synthetic endeavor toward diastereomers 14 enabled the structure assignment of isomer 3; the proposed biosynthetic pathway for marine oxylipins also supports the result.