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. Author manuscript; available in PMC: 2018 Sep 27.
Published in final edited form as: Chem Rev. 2017 Jun 5;117(18):11894–11951. doi: 10.1021/acs.chemrev.7b00022

Figure 20.

Figure 20

(A) Site-selective mesylation of rhamnose (104). The catalyst is selective for cis-1,2-diols. (B) Imidazole-2-methoxyoxazolidine catalysts. (C) Selectivity patterns for the mesylation of 104 with various catalysts. (D) A proposed intermediate that forms upon addition of one of the cis-1,2-alcohols into the oxazolidine. The imidazole will next deliver the mesylate via to the free alcohol. (E) Site-selective mesylation of mupirocin methyl ester (108). (F) Site-selective modification of digoxin (111).149