Contiguously substituted cyclooctane polyols. Configurational assignments via 1H NMR correlations and symmetry considerations

Gustavo Moura, Leo A. Paquette

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Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)7663-7670
Number of pages8
JournalJournal of Organic Chemistry
Volume73
Issue number19
DOIs
Publication statusPublished - Oct 3 2008

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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