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Contiguously Substituted Cyclooctane Polyols. Configurational Assignments via 1 H NMR Correlations and Symmetry Considerations

2008; American Chemical Society; Volume: 73; Issue: 19 Linguagem: Inglês

10.1021/jo801443d

1520-6904

Gustavo Moura‐Letts, Leo A. Paquette,

Phosphorus compounds and reactions

More advanced oxidation of the cyclooctadienol shown, readily available in enantiomerically pure form from d-glucose, has given rise to a series of intermediates whose relative (and ultimately absolute) configuration was assigned on the basis of 1H/1H coupling constant analysis. The selectivities that were deduced in this manner were drawn from the sequential application of CrO3 oxidation in tandem with Luche reduction, two-step NMO-promoted osmylations bracketed by acetonide formation, and wholesale deprotection. The stereoselectivities of these reactions were traced by 1H NMR spectroscopy, and the stereochemical assignments were confirmed by the presence or absence of symmetry in the final cyclooctane polyols (four shown) generated in this investigation.