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Oxidative cleavage of N-acetyl-neuraminic acid (Neu5Ac, 1) leads to the open chain octonic acid (ADOA, 2), which under various conditions is transformed into an acyclic acid or ester or into… Click to show full abstract
Oxidative cleavage of N-acetyl-neuraminic acid (Neu5Ac, 1) leads to the open chain octonic acid (ADOA, 2), which under various conditions is transformed into an acyclic acid or ester or into a six- or five-membered octonic acid lactone and lactam, respectively. All reactions proceed with high selectivity and in good yields. Strikingly, a simple switch of reaction conditions from basic to acidic catalysis leads to a complete switch in regioselectivity during a crucial cyclization step.
Keywords:
octonic acid;
dideoxy octonic;
synthesis dideoxy;
acid cyclic;
cyclic acyclic;
acid
Journal Title: Organic letters
Year Published: 2020
Link to full text (if available)
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Journal Title: Organic letters
Year Published: 2020
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!