2,3-O-Isopropylidene-d-glyceraldehyde reacts with dimethylphosphine oxide in the presence of triethylamine to give separable (1S,2R)-and (1R,2R)-1-dimethylphosphinylgrycerol (65 :35), from which the (1R) and (1S) title compounds are respectively derived via 1-O-mesyl and 1-azido derivatives. The corresponding 1-dimethoxyphosphinylglycerols are similarly prepared. Structural and conformational assignments of these products are made on the basis of the 1H NMR data and [α]D values.
-N-Benzyloxy-2-diethoxyphosphoryl)pent-4-enamide (6) was prepared from ethyl diethoxyphosphorylacetate in a 3-step sequence. Oxidative cleavage of the terminal olefin of 6 with osmium tetroxide and sodium periodate afforded 1-benzyloxy-3-diethoxyphosphoryl-5-hydroxy-2-pyrrolidone (7). The first synthesis of racemic SF-2312 was achieved by treatment of 7 with trimethylsilyl bromide, followed by hydrogenolysis.Phosphonic acid antibiotics containing a hydroxamic acid function have attracted considerable interest in medicinal chemistry because of their antimicrobial activities. For example, fosmidomycin (1) 1 and its N-acetyl analog FR-900098 (2), 2 isolated from Streptomyces lavendulae and S. rubellomurinus sp., respectively, were found to be potent inhibitors for the 1-deoxy-D-xylulose 5-phosphate reductoisomerase.
3In recent years, a number of analogs of these compounds have been synthesized owing to the investigation of structure-activity relationships and development of antimalarial agents. 4,5 Meanwhile, SF-2312 (3), a phosphonic acid antibiotic active against Gram-positive and Gram-negative bacteria, was isolated from Micromonospora sp. 6,7 Despite its unique structure in having a 1,5-dihydroxy-2-pyrrrolidone ring, attempts at preparation of 3 and the assignment of the stereochemistry have not been made so far. We describe herein the first, efficient synthesis of racemic SF-2312 (3) as a preliminary study for asymmetric synthesis of 3.
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