Concise syntheses of (-)-and (+)-syringolide 1 and (-)-Δ7-syringolide 1

C Zeng, SL Midland, NT Keen…

Index: Zeng, Chun-Min; Midland, Sharon L.; Keen, Noel T.; Sims, James J. Journal of Organic Chemistry, 1997 , vol. 62, # 14 p. 4780 - 4784

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Citation Number: 18

Abstract

(-)-and (+)-Syringolide 1 have been synthesized from 2, 3-O-isopropylidene-β-threo- pentulofuranose (1), which was readily prepared from d-or l-xylose, respectively. Condensation of 1 with 3-oxooctanoic acid and treatment of the ester with TFA: H2O (9: 1) produced syringolide 1 in 6.3% yield for the two steps. According to the same synthetic route by replacing 3-oxooctanoic acid with 3-oxo-7-octenoic acid,(-)-Δ7-syringolide 1 was ...