An enantioselective synthesis of N-methylfucosamine via tandem C-C/C-O bond formation

Dalibor Sames, Robin L Polt

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Optically pure D-(+)-N-methylfucosamine (8) has been synthesized from a TBDMS-protected methyl L-serinate benzophenone Schiff base (O'Donnell's Schiff base, 1) in seven steps in 13% overall yield. Efficient construction of the requisite amino triol acetate 3a with the proper stereochemical configuration is accomplished in two steps with a chelation-controlled reduction - alkylation reaction using |Bu2AlH·Al-iBu3/E-LiCH=CHCH3, followed by oxidation with OsO4. Conversion of the Schiff base to the N-benzhydryl protecting group and methylation (Eschweiler-Clark) is accomplished in one pot with NaCNBH3 in the presence of H2C=O. Deprotection and oxidation of the primary alcohol, followed by deacetylation with KCN, provided the desired product 8.

Original languageEnglish (US)
Pages (from-to)4596-4601
Number of pages6
JournalJournal of Organic Chemistry
Issue number16
Publication statusPublished - 1994


ASJC Scopus subject areas

  • Organic Chemistry

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