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1 H and 13 C NMR assignments for lanostan‐3β‐ol derivatives: Revised assignments for lanosterol
Author(s) -
Emmons Gary T.,
Wilson William K.,
Schroepfer Jr George J.
Publication year - 1989
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260271103
Subject(s) - lanosterol , lanostane , chemistry , acetylation , diol , stereochemistry , chemical shift , organic chemistry , triterpene , biochemistry , medicine , alternative medicine , sterol , pathology , cholesterol , gene
1 H and 13 C NMR assignments are presented for 30 oxygenated lanostane derivatives, including lanosterol, dihy‐drolanosterol, 7‐ketolanosterol, agnosterol, 24,25‐epoxylanosterol, 8α,9α‐epoxylanostan‐3β‐ol, three 15‐oxygenated derivatives of lanost‐7‐en‐3β‐ol, lanostane‐3β,7α‐diol, lanostane‐3β,9α‐diol and their acetates. These assignments, which were largely determined by a combination of DEPT, one‐boad and long‐range 13 C 1 H chemical shift correlation and lanthanide‐induced shift experiments, are not dependent on previously reported assignments, several of which were found to be incorrect. 1 H and 13 C acetylation shifts for lanostan‐3β‐ols were sufficiently invariant among the sterols studied that they were useful for assigning carbons in rings A and B. The acetylation shifts reported for lanostan‐3β‐ols were extended and partially revised.