Abstract
First stereoselective total synthesis of an anti-fouling agent, C2-symmetric natural macrolide trichobotryside A
Highlights
Marine organisms have been widely explored for potential bioactive lead compounds, within many different chemical classes of compounds such as peptides, terpenoids, steroids, alkaloids, macrolides and other polyketide lactones.[1,2,3] The macropolylides, essentially 16-membered macrodiolides such as pyrenophorol, pyrenophorin, and vermiculin (Figure 1) have strong antifungal and anthelmintic activity
As part of our regular research program in synthesis of biologically active natural and synthetic compounds, we demonstrate the first stereoselective total synthesis of the 16-membered macrodiolide trichobotryside A
As envisaged in the retrosynthetic analysis (Scheme 1) trichobotryside A could be reached from the monomer 18 after Wittig, Sharpless epoxidation and cross metathesis
Summary
Marine organisms have been widely explored for potential bioactive lead compounds, within many different chemical classes of compounds such as peptides, terpenoids, steroids, alkaloids, macrolides and other polyketide lactones.[1,2,3] The macropolylides, essentially 16-membered macrodiolides such as pyrenophorol, pyrenophorin, and vermiculin (Figure 1) have strong antifungal and anthelmintic activity. The residue was purified by column chromatography over silica gel (60-120 mesh) by eluting with hexanes:EtOAc (85:15) mixture to afford allylic alcohol 6 (3.28 g, 14.9 mmol, 76%) (dr 95:5) as a colorless liquid. The crude product was purified by column chromatography using silica gel (60-120 mesh) by eluting with hexane/EtOAc (9:1) mixture to give ester compound 10 (1.95 g, 86%) as pale yellow liquid (95:5, E/Z).
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