1430812-92-2Relevant academic research and scientific papers
Total synthesis of epicoccamides A and D via olefin cross-metathesis
Yajima, Arata,Kawajiri, Akihiro,Mori, Ayaka,Katsuta, Ryo,Nukada, Tomoo
, p. 4350 - 4354 (2014/07/22)
Epicoccamides A and D were synthesized through a route that utilizes fragment coupling via olefin cross-metathesis as a key step. The right-hand segment of the epicoccamides was synthesized by a tandem O-acylation-migration reaction, and the left-hand segments were stereoselectively synthesized through a modified version of Crich's β-selective mannosylation. The previously assigned absolute configuration of the epicoccamide D was confirmed, and that of epicoccamide A was assigned as (5S,2′S) based on the NMR and CD spectra. This Letter provides the first example of the total synthesis of epicoccamide A.
Total synthesis of virgineone aglycone and stereochemical assignment of natural virgineone
Yajima, Arata,Ida, Chieko,Taniguchi, Kayoko,Murata, Shoko,Katsuta, Ryo,Nukada, Tomoo
, p. 2497 - 2501 (2013/06/27)
The first total synthesis of virgineone aglycone has been achieved employing the tandem O-acylation-migration reaction and the olefin cross-metathesis as key steps for fragment couplings. The left-hand segment of virgineone was also synthesized. The absolute configuration of the reported virgineone aglycone was determined to be (2S,7RS,26S) based on NMR analyses and the specific rotation values of the synthetic compounds. The absolute configuration of the natural virgineone was presumed to be (2S,7S,26S) based on NMR analyses of the synthetic virgineone aglycone.
