76343-92-5Relevant academic research and scientific papers
On the Chemistry of Latrunculins A and B
Blasberger, Dina,Carmely, Shmuel,Cojocaru, Miriam,Spector, Ilan,Shochet, Nava R.,Kashman, Yoel
, p. 1171 - 1188 (2007/10/02)
The chemical behavior of latrunculins A (1) and (B) (Lat A and B) under a variety of reaction conditions is described.The combination of the macrolide, the THP-lactol, and the 2-thiazolidinone rings was found to result on interesting unpredicted chemical transformations.The structures of two new Lats, 6,7-epoxy-Lat A (3) and Lat M (4) isolated from Latrunculia magnifica, are discussed.
Latrunculins: NMR study, two new toxins and a synthetic approach
Kashman,Groweiss,Lidor,et al.
, p. 1905 - 1914 (2007/10/02)
A complete 1H and 13C NMR assignment of one of the latrunculins (B) was accomplished with the aid of 2D NMR COSY and CH shift-correlation experiments. The various H-H coupling constants have been determined and a conformation of the macrolide and the tetrahydropyran (THP) ring suggested on basis of the J-values and measured NOE's. The absolute configuration of latrunculin-A(1) was determined on the grounds of its earlier X-ray analysis, and a chemical degradation to a known compound. Two novel latrunculins, -C(3) and -D(4), were isolated from the Red Sea sponge L. magnifica and their structures elucidated. Starting with L-cysteine a synthon for the latrunculins has been synthesized.
Marine Toxins of Latrunculia magnifica
Groweiss, Amiram,Shmueli, Uri,Kashman, Yoel
, p. 3512 - 3516 (2007/10/02)
Latrunculins A (1) and B (2) are the major extractable toxins of Latrunculia magnifica, constituting up to O.35 percent of the dry weight of the sponge.The structure of the compounds was determined by detailed spectral analysis, some minor chemical transformations, and X-ray crystallography.The latrunculins are the first-known 2-thiazolidinone-bearing marine macrolides.They were found to cause major alterations in specific cytoskeletal proteins.A retrosynthesis of the new compounds is suggested.
