An enantioselective total synthesis of pseudodehydrothyrsiferol has been accomplished. The synthetic sequence highlights formation of the highly strained tetrahydropyran C-ring by a Mitsunobu-type S(N)2 reaction with an oxygen nucleophile.
[structure: see text] Enantioselective synthesis of eurylene, 14-deacetyl eurylene, and their 11-epimers was achieved. The characteristic structural feature of these compounds is two tetrahydrofuran (THF) rings substituted in different stereochemistry. The synthetic approach involves nonstereoselective THF ring formation to afford both segments from a common precursor. We also investigated their ionophoric nature and cytotoxicity. The complexation of these compounds with K(+) might be related to their cytotoxic activity.
Other bioactive products U 1300Total Synthesis of Pseudodehydrothyrsiferol. -The highly strained tetrahydropyran C-ring of title compound (IV) is built up by a Mitsunobu-type S N 2 reaction with the Tsunoda reagent. The ring closure proceeds with complete inversion of the C-14 configuration. -(HIOKI*, H.; MOTOSUE, M.; MIZUTANI, Y.; NODA, A.; SHIMODA, T.; KUBO, M.; HARADA, K.; FUKUYAMA, Y.; KODAMA, M.; Org. Lett. 11 (2009) 3, 579-582; Fac. Pharm. Sci., Tokushima Bunri Univ., Yamashiro, Tokushima 770, Japan; Eng.) -Lindner 25-203
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