Add time:08/29/2019         Source:sciencedirect.com

Publisher SummaryIn 1990, Anke, Steglich, and coworkers reported the isolation and structure elucidation of three compounds from the fungus, Xerula melanotricha—xerulin, dihydroxerulin, and xerulinic acid. These are structurally closely related substances; Xerulin and dihydroxerulin were characterized as 10:90—35:65 mixtures, whereas xerulinic acid was obtained in pure form. Each of the three compounds suppressed the biosynthesis of cholesterol. If the γ-(α-hydroxyalkyl) butenolide substrates are diastereomerically pure and if dehydrations could be conducted anti-selectively, route to 7- alkylidenebutenolides would be both stereoselective and stereospecific. Stereopure γ-(α-hydroxyalkyl) butenolides would lead to γ-alkylidenebutenolides with a Z-configuration exclusively. The stereoselectivities would depend only on the relative configurations at centers C-γ and C-1 and not on their absolute configurations. An interesting variant of such γ-alkylidenebutenolide syntheses has promised to be stereoselective and “stereodivergent” rather than stereospecific. This modification would require just one γ-(α-hydroxyalkyl) butenolide diastereomer.

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