Tetrahedron Letters

Synthesis of optically active leukotriene (SRS-A) intermediates

N Cohen, BL Banner, RJ Lopresti

文献索引：Cohen, Noal; Banner, Bruce L.; Lopresti, Rocco J. Tetrahedron Letters, 1980 , vol. 21, p. 4163 - 4166

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被引用次数: 23

摘要

-Araboascorbic acid was treated with diazotized p-toluidine (NaNO 2 /aqueous H 2 SO 4 ) at 0°C giving (−)-(3 - )-mono(tetrahydro-4-hydroxy-2-oxo-3-furanyl)ester 2-(4-methylphenyl)hydrazide of ethanedioic acid 6 (55%; mp 187-9°C d., [α] 25 D −59.3° (c 0.5,EtOH)), which, when hydrolyzed in boiling water, afforded D-erythronolactone 6 (74%; mp 97.5–99°C, [α] 25 D −71.4° (c 0.5,H 2 O)). The acetonide 7,8 was then prepared (2,2-dimethoxypropane-acetone-p-TsOH, ...