Abstract
The paper describes the first total synthesis of natural varioxiranol A by chiral pool approach and confirmation of its absolute configuration by single-crystal X-ray analysis. The target varioxiranol A and its 4-epimer were obtained after 10 steps from single and available chiral source 1,2-O-isopropylidene-d-glyceraldehyde in an overall yield of 10% and 6%, respectively. A synthetic strategy based on the Julia–Kocieński coupling reaction between aromatic sulfone and corresponding aldose derivative makes it possible to prepare other interesting polyketide derivatives (varioxiranols B-G, varioxirane, varioxiranediols).
Highlights
The fungus Emericella variecolor [1] is considered as a promising source of interesting bioactive compounds
Johnstone and used for the first time in the manuscript dealing with the synthesis [4]
In 2002, Malmstrøm et al [5] reported the isolation of benzyl alcohols, prenylxanthones, and cyclopentanones from a strain of E. variecolor derived from a Caribbean sponge
Summary
The fungus Emericella variecolor [1] is considered as a promising source of interesting bioactive compounds. In 2002, Malmstrøm et al [5] reported the isolation of benzyl alcohols (varitriol 3, varioxirane 2), prenylxanthones (shamixanthone, varixanthone, tajixanthone), and cyclopentanones from a strain of E. variecolor derived from a Caribbean sponge. Seven new polyketide derivatives with benzyl alcohol structural motif, namely varioxiranols A–G, isolated by chemical examination of a sponge (Cinachyrella sp.)-associated E. variecolor fungus and tested for lipid-lowering effects against oleic acid, elicited lipid accumulation in HepG2 liver cells. Among these secondary metabolites, varioxiranol A 4 exerted inhibition activity and showed no toxicity [6].
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