Synthetic Studies toward Mannopeptimycin-E: Synthesis of the O-Linked Tyrosine 1,4-α,α-manno,manno-Pyranosyl Pyranoside
- 21 March 2006
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (8) , 1605-1608
- https://doi.org/10.1021/ol060254a
Abstract
The enantioselective synthesis of the C-4‘ acylated 1,4-α,α-manno,manno-disaccharide fragment of mannopeptimycin-E has been achieved in seven steps from d-tyrosine. The route relies upon diastereoselective palladium-catalyzed glycosylation, diastereoselective reduction, and diastereoselective bis-dihydroxylation. The efficiency of the synthesis is demonstrated by the high overall yield (37%) and the preparation of various analogues.Keywords
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