Concise and Highly Stereocontrolled Synthesis of 1-Deoxygalactonojirimycin and Its Congeners Using Dioxanylpiperidene, a Promising Chiral Building Block
journal contributionposted on 19.06.2003, 00:00 by Hiroki Takahata, Yasunori Banba, Hidekazu Ouchi, Hideo Nemoto
A concise and stereoselective synthesis of the chiral building block, dioxanylpiperidene 4 as a precursor for deoxyazasugars, starting from the Garner aldehyde 5 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring is described. The asymmetric synthesis of 1-deoxygalactonojirimycin and its congeners 1−3 was carried out via the use of 4 in a highly stereocontrolled mode.
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DeoxygalactonojirimycinmetathesiRCMstereoselective synthesisDioxanylpiperidenepiperidine ringstereocontrolled modedeoxygalactonojirimycinPromising Chiral Building BlockCongenerdioxanylpiperidene 4congenerStereocontrolled Synthesisconstructiondeoxyazasugarchiral building blockConciseprecursorGarner aldehyde 5