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Structure elucidation by NMR spectroscopy of saccharolidin A, a novel antiparasitic macrolide from Saccharothrix aerocolonigenes

✍ Scribed by Alistair G. Swanson; Robert A. Monday; David A. Perry

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
678 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The structure of saccharolidin A, C~38~H~60~O~9~, 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.

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