01458nas a2200169   4500008004100000022001400041245007700055210006900132260007100201300001400272490000700286520082200293100002301115700002301138700001901161856010801180       2005                        eng d  a0022-326300aSynthesis of eupomatilone-6 and assignment of its absolute configuration0 aSynthesis of eupomatilone6 and assignment of its absolute config  a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcNOV  a9658-96610 v703 a<p>[GRAPHICS] The Zn-mediated Barbier reaction of the biarylaldehyde 8 with crotyl bromide followed by hydroboration and oxidation provided the gamma-butyrolactones 4 and 5. The stereoselective installation of methyl group at C-3 by using LiHMDS and MeI completed the synthesis of racemic eupomatilone-6 (2) and its diastereomer 3. The spectroscopic data of 2 was in fall agreement with reported spectra of natural product, thus confirming the revised relative configuration of eupomatilone-6. Similarly, an optically active (3R,4R,5S)-isomer of eupomatilone-6 (23) was prepared in which the aldol reaction with thiazolidinethione as a chiral auxiliary was employed as a key step. On the basis of the spectroscopic data and optical rotation values of 23, the absolute configuration of eupomatilone-6 was proposed.</p>1 aGurjar, Mukund, K.1 aKarumudi, Bhargava1 aRamana, C., V.  uhttps://library.ncl.res.in/content/synthesis-eupomatilone-6-and-assignment-its-absolute-configuration-1