22644-28-6Relevant articles and documents
Synthesis and complete structure determination of a sperm-activating and -attracting factor isolated from the ascidian ascidia sydneiensis
Watanabe, Tomohiro,Shibata, Hajime,Ebine, Makoto,Tsuchikawa, Hiroshi,Matsumori, Nobuaki,Murata, Michio,Yoshida, Manabu,Morisawa, Masaaki,Lin, Shu,Yamauchi, Kosei,Sakai, Ken,Oishi, Tohru
, p. 985 - 997 (2018/05/04)
For the complete structure elucidation of an endogenous sperm-activating and -attracting factor isolated from eggs of the ascidian Ascidia sydneiensis (Assydn-SAAF), its two possible diastereomers with respect to C-25 were synthesized. Starting from ergosterol, the characteristic steroid backbone was constructed by using an intramolecular pinacol coupling reaction and stereoselective reduction of a hydroxy ketone as key steps, and the side chain was introduced by Julia-Kocienski olefination. Comparison of the NMR data of the two diastereomers with those of the natural product led to the elucidation of the absolute configuration as 25S; thus the complete structure was determined and the first synthesis of Assydn-SAAF was achieved.
Cobalt versus Osmium: Control of Both trans and cis Selectivity in Construction of the EFG Rings of Pectenotoxin 4
Roushanbakhti, Ahria,Liu, Yifan,Winship, Paul C. M.,Tucker, Michael J.,Akhtar, Wasim M.,Walter, Daryl S.,Wrigley, Gail,Donohoe, Timothy J.
supporting information, p. 14883 - 14887 (2017/10/24)
Catalytic oxidative cyclisation reactions have been employed for the synthesis of the E and F rings of the complex natural product target pectenotoxin 4. The choice of metal catalyst (cobalt- or osmium-based) allowed for the formation of THF rings with either trans or cis stereoselectivity. Fragment union using a modified Julia reaction then enabled the synthesis of an advanced synthetic intermediate containing the EF and G rings of the target.
Facile synthesis of versatile enantioenriched α-substituted hydroxy esters through a Bronsted acid catalyzed kinetic resolution
Qabaja, Ghassan,Wilent, Jennifer E.,Benavides, Amanda R.,Bullard, George E.,Petersen, Kimberly S.
, p. 1266 - 1269 (2013/05/09)
An efficient synthesis of enantioenriched α-substituted γ-hydroxy esters via a kinetic resolution event is described. Bulky racemic esters in the presence of a chiral Bronsted acid selectively lactonize to yield a recoverable enantioenriched hydroxy ester and lactone. These esters are highly versatile building blocks that can readily be converted to synthetically useful materials.