TY - JOUR
T1 - Synthesis and complete structure determination of a sperm-activating and -attracting factor isolated from the ascidian ascidia sydneiensis
AU - Watanabe, Tomohiro
AU - Shibata, Hajime
AU - Ebine, Makoto
AU - Tsuchikawa, Hiroshi
AU - Matsumori, Nobuaki
AU - Murata, Michio
AU - Yoshida, Manabu
AU - Morisawa, Masaaki
AU - Lin, Shu
AU - Yamauchi, Kosei
AU - Sakai, Ken
AU - Oishi, Tohru
N1 - Funding Information:
This work was partly supported with grants from JST ERATO Lipid Active Structure.
Publisher Copyright:
© 2018 American Chemical Society and American Society of Pharmacognosy.
PY - 2018/4/27
Y1 - 2018/4/27
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85046079122&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85046079122&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.7b01052
DO - 10.1021/acs.jnatprod.7b01052
M3 - Article
C2 - 29589931
AN - SCOPUS:85046079122
SN - 0163-3864
VL - 81
SP - 985
EP - 997
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 4
ER -