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Total Synthesis of the Reputed Structure of Alcyonin and Reassignment of Its Structure

2003; American Chemical Society; Volume: 5; Issue: 9 Linguagem: Inglês

10.1021/ol034384k

1523-7060

Olivier Corminboeuf, Larry E. Overman, Lewis D. Pennington,

Synthetic Organic Chemistry Methods

Introduction of the C4 hydroxyl group by an epoxy ester rearrangement is a pivotal step in the first total synthesis of the purported structure of alcyonin. As the spectral data for diol acetate 3 do not match those reported for alcyonin, the structure of this marine diterpene must be revised. Reexamination of NMR spectra, MS data, and chemical transformations of natural alcyonin suggests that the structure of this marine metabolite is allylic peroxide 15.