191285-49-1Relevant academic research and scientific papers
Concise Syntheses of (-)- and (+)-Syringolide 1 and (-)-Δ7-Syringolide 1
Zeng, Chun-Min,Midland, Sharon L.,Keen, Noel T.,Sims, James J.
, p. 4780 - 4784 (2007/10/03)
(-)- 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 prepared in 5.8% yield. Primary β-keto esters of arabinulose and fructose were also prepared to test the selectivity of the biomimetic cyclization to form syringolide analogs.
