Synthetic studies on antibiotic validamycins. Part 12. Total synthesis of (+)-validamycin B and (+)-validoxylamine B
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 2675-2680
- https://doi.org/10.1039/p19880002675
Abstract
The first complete synthesis of validamycin B (1a) and validoxylamine B (2a) is reported; coupling of the epoxide (12) and the partially protected derivative (16) of (+)-valienamine, followed by deprotection, gives (1a), which was identified from the 1H n.m.r. spectrum of its totally O-acetylated derivative (1b). Alternatively, coupling of the epoxide (24) with the amine (16) affords compound (25), the structure of which can be established by converting (25) into validoxylamine B nona-O-acetate (2b). The appropriately protected amine (29) derived from (25) is glycosylated, followed by deprotection and acetylation, to give (1b).Keywords
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