2024-03-29T07:13:00Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/582652022-11-17T02:08:08Zhdl_2115_20039hdl_2115_116A stereoselective method for the construction of the C8′–O–C6″ ether of nigricanoside-A: synthesis of simple models for the C20 lipid chain/galactosyl glycerol segmentKinashi, Naoto1000020222268Fujiwara, KenshuTsunoda, TakayukiKatoono, RyoKawai, Hidetoshi1000070202132Suzuki, Takanoriopen accessNatural product synthesisMonogalactosyl diacyl glycerolIreland–Claisen rearrangementEther lipidStereoselective synthesis430A method for the stereoselective construction of the C8′–O–C6″ ether of nigricanoside-A, an antimitotic natural product from the green alga Avrainvillea nigricans, has been developed based on chirality-transferring Ireland–Claisen rearrangement. The method was successfully applied to the synthesis of simple models for the C20 lipid chain/galactosyl glycerol segment of the natural product.Elsevier2013-08-21engjournal articleAMhttp://hdl.handle.net/2115/58265https://doi.org/10.1016/j.tetlet.2013.06.0850040-4039Tetrahedron Letters543445644567https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/58265/1/TL_54_p4567-.pdfapplication/pdf252.13 KB2013-08-21