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Synlett 1995; 1995(3): 285-288
DOI: 10.1055/s-1995-4937
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Synthesis of Segment C of Tautomycin

Yimin Jiang, Yoshiyasu Ichikawa, Minoru Isobe*
  • *Laboratory of Organic Chemistry, School of Agricultural Sciences, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
31 December 2000 (online)

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Synthesis of Segment C of tautomycin was accomplished from 2 D-sugar derivatives. New heteroconjugate addition strategy allowed stereocontrolled syntheses of the 2 sub-segments, C-1 and C-2, and 3 other diastereoisomers of the latter. Sub-segments were coupled between sulfone carbanion and epoxide electrophile to furnish the spiro ring moiety of the target compound.

tautomycin - segment C - heteroconjugate addition - pseudoenantiomer - enantiomer - sulfone