1489263-06-0Relevant academic research and scientific papers
Stereochemical assignment of topsentolide C2 by stereodivergent synthesis of its four diastereomers
Towada, Ryo,Kurashina, Yusuke,Kuwahara, Shigefumi
, p. 6878 - 6881 (2013)
Four diastereomers of topsentolide C2, a cytotoxic 9-membered lactone isolated from the marine sponge Topsentia sp., were synthesized stereodivergently from a common chiral seco acid by the combined use of the Yamaguchi and Mitsunobu lactonizations. Comparison of the NMR spectra of the four diastereomers with those of an authentic sample of topsentolide C2 led to the stereochemical determination of topsentolide C2 as 8R, 11S and 12S.
Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter
Towada, Ryo,Kuwahara, Shigefumi
, p. 3774 - 3781 (2014/05/20)
The first total synthesis of the marine-derived cytotoxin topsentolide A2, which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C2, from a synthetic intermediate of topsentolide A2 was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide A2 with HCl/MeOH brought about its quantitative conversion into topsentolide C2.
