作者: Olivier Corminboeuf , Larry E. Overman , Lewis D. Pennington
DOI: 10.1021/JO9010156
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摘要: Enantioselective total syntheses of briarellin E (12) and F (13), as well the structure originally proposed for cladiellin diterpene alcyonin (10), have been realized. Comparison spectral data synthetic 10, natural alcyonin, cladiellisin (33), cladiellaperoxide (34), chemical transformations 10 suggest that this coral metabolite is allylic peroxide 11. The unified approach detailed herein can be used to access both C4-deoxygenated C4-oxygenated cladiellins briarellins. central step in these acid-promoted condensation (Z)-α,β-unsaturated aldehydes 17 with cyclohexadienyl diols 18 form intermediates 16 incorporating hexahydroisobenzofuran core five stereocenters marine diterpenes (Scheme 1).