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Enantioselective Synthesis of Nabscessin C
Chun-Wei Yeh1, Chia-Chi Feng1, Pei-Lin Chen2
1Department of Chemistry, National Central University, 300 Jhong-Da Road, Jhong-Li, Taoyuan 320317, Taiwan.
Abstract:
Enantioselective synthesis of nabscessin C (1), an aminocyclitol amide with antimicrobial activity, is reported. Starting from myo-inositol, (+)-nabscessin C was synthesized in 12 isolation steps. Desymmetrization of 2-deoxygenated 4,6-dibenzylinositol was achieved using lipase from porcine pancreas (PPL), and the stereochemistry was established by X-ray crystallography. This method has the potential for synthesizing other cyclitol-derived compounds.
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