Synthesis of amykitanose, an O-carbamoyl sugar component of the antibiotic amycolamicin
Meguro, Yasuhiro 1Taguchi, Yuka 1Enomoto, Masaru 1Kuwahara, Shigefumi1
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作者信息
1. Tohoku Univ
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Abstract
The first synthesis of amykitanose, an O-carbamoyl pyranose component of the potent broad-spectrum antibiotic amycolamicin, has been accomplished from L-fucose in eight steps. The key transformations involve a stereochemical inversion at the C2 asymmetric center of an L-fucose derivative via an oxidation/reduction sequence, a regioselective installation of the 3-acetoxy functionality by acid-promoted hydrolysis of a cyclic orthoester, and a titanium tetrabromide-mediated hydrolysis of a penultimate glycoside intermediate. (C) 2022 Elsevier Ltd. All rights reserved.
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Elsevier