ISSN:
0749-1581
Keywords:
2D NMR
;
Saccharolidin A
;
Natural product
;
Hygrolide
;
Assignment strategy
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The structure of saccharolidin A, C38H60O9, a macrolide with antiparasitic properties isolated from Saccharothrix aerocolonigenes, was determined by two-dimensional NMR using a fragment-directed approach. Complete elucidation of the structure required concerted application of a range of homo- and heteronuclear experiments (TOCSY, ROESY, HMQC, HMBC, HMQC-TOCSY). Saccharolidin A is related to the hygrolides but contains a number of unique features which distinguish it from previously reported members of this family. It is unsubstituted on C-2 and contains both a 1,3-dioxepane ring and an unsubstituted n-pentyl side-chain. The relative stereochemistry within each of the three groups of contiguous chiral centres has been determined.
Additional Material:
11 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260301317
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