A divergent route to 3-amino-2,3,6-trideoxysugars including branched sugar: Synthesis of vancosamine, daunosamine, saccharosamine, and ristosamine

Takayuki Doi, Kazuaki Shibata, Atsushi Kinbara, Takashi Takahashi

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Four 3-amino-2,3,6-trideoxysugars were synthesized by a divergent route from a single enone 9a. The Migita-Stille coupling introduced a methyl group at the 3-position. Stereoselective reduction of enone and the Mitsunobu reaction provided both β- and α-hydroxy groups at the 4-position. Stereospecific radical cyclization of the C4 carbamoyl moiety furnished the desired 5a, 5b and 6a, 6b, respectively.

Original languageEnglish
Pages (from-to)1372-1373
Number of pages2
JournalChemistry Letters
Volume36
Issue number11
DOIs
Publication statusPublished - 2007 Nov 5
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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