37 Sulfobacin類の全合成(口頭発表の部)
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Sulfobacins A (1) and B (2), novel von Willebrand factor (vWF) receptor antagonists, have been isolated by Kamiyama et al.^1 from the culture broth of Chryseobacterium sp. (Flavobacterium sp.) NR 2993 in a soil sample collected in Iriomote Island, Okinawa Prefecture, Japan. Sulfobacin A (1) was also isolated by Kobayashi et al.^2 as flavocristamide B from Flavobacterium sp. in the marine bivalve Cristria plicata collected in Ishikari Bay, Hokkaido, Japan. Sulfobacins A (1) and B (2) inhibit the binding of vWF to the GPIb/IX receptors in a competitive manner with IC_<50>s of 0.47 and 2.2 μM, respectively.^<1a> Furthermore, sulfobacin A (1) was found to have inhibitory activity against DNA polymerase α. 2 We now wish to report the first total synthesis of sulfobacins in an effective and stereoselective manner. The left fragment 4 was obtained through the asymmetric hydrogenation of the corresponding β-keto ester 9 with a chiral Ru(II) catalyst atmospheric pressure according to the Genet's method. The right fragment 5 was constructed by the asymmetric aldol reaction using the Schiff base derived from (+)-2-hydroxy-3-pinanone ((+)-HyPN, 11). Sulfobacins were prepared from the corresponding thioacetates (17 and 24), which were constructed by coupling the left fragment 4 with the right fragment 5 by use of diethyl phosphorocyanidate (DEPC, (C_2H_5O)_2P(O)CN) as a coupling reagent The synthetic sulfobacins were identical with the natural ones in every respect (IR, ^1H NMR, ^<13>C NMR spectra, [α]_D and TLC). Thus we have completed the first total synthesis of sulfobacins.
- 天然有機化合物討論会の論文
- 1998-08-31
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