215958-93-3Relevant academic research and scientific papers
Revised structure, synthesis and absolute configuration of hippospongic acid A
Hioki, Hideaki,Hamano, Masayo,Mimura, Yumi,Kodama, Mitsuaki,Ohta, Shinji,Yanai, Mihoko,Ikegami, Susumu
, p. 7745 - 7746 (1998)
The structure of hippospongic acid A was reinvestigated and new evidence supporting the revised structure previously proposed was obtained. The structure, including absolute configuration, was established by the enantioselective synthesis.
Enantioselective total synthesis and absolute stereostructure of hippospongic acid A
Hioki, Hideaki,Ooi, Hidenori,Hamano, Masayo,Mimura, Yumi,Yoshio, Suzuyo,Kodama, Mitsuaki,Ohta, Shinji,Yanai, Mihoko,Ikegami, Susumu
, p. 1235 - 1246 (2007/10/03)
A compound having the structure proposed for hippospongic acid A, a triterpene that specifically inhibits gastrulation of starfish embryos, was synthesized enantioselectively. The synthetic compound was not identical to the natural product. Comparison of the NMR spectra of the natural and synthetic compounds led us to propose an alternative structure, which was confirmed by enantioselective synthesis. The present synthesis established that the natural product has the (R)-configuration.
