66873-39-0Relevant academic research and scientific papers
Total synthesis of thyrsiferyl 23-acetate, a specific inhibitor of protein phosphatase 2A and an anti-leukemic inducer of apoptosis
Gonzalez, Isabel C.,Forsyth, Craig J.
, p. 9099 - 9108 (2007/10/03)
A convergent synthetic entry to the squalenoid polyether system has been developed and applied to the biologically active marine natural products thyrsiferyl 23-acetate (1a), thyrsiferol (1b), thyrsiferyl 18-acetate (1c), and thyrsiferyl 18,23-diacetate (
Total Syntheses of (+)-Thyrsiferol, (+)-Thyrsiferyl 23-Acetate, and (+)-Venustatriol
Hashimoto, Masaru,Kan, Toshiyuki,Nozaki, Koji,Yanagiya, Mitsutoshi,Shirahama, Harushia,Matsumoto, Takeshi
, p. 5088 - 5107 (2007/10/02)
The first total syntheses of (+)-thyrsiferol (1), (+)-thyrsiferyl 23-acetate (3), and (+)-venustatriol (5) have been accomplished in a stereoselective manner.An effective synthetic scheme to construct the BC ring system, which adopts a chair/twist-boat conformation, was first developed by means of a model study.This method involves stereoselective formation of the strained C ring by intramolecular attack of the C7-hydroxyl group at the C3-postion of the 2,3-epoxy alcohol, employing titanium tetraisopropoxide as an acidic activator.Based on the information accumulated in the model study and retrosynthetic considerations, the total syntheses of 1,3, and 5 were performed in the sequence of (1) construction of the BC ring system equipped with a C1-C6 carbon unit, (2) elongation of the C17-C24 carbon chain, (3) formation of a D ring through the stereoselective epoxidation of the 4-en-1-ol system and successive cyclization, and (4) construction of the A ring by bromonium ion induced cyclization of the 4-en-1-ol system.
Cytotoxic Squalene-Derived Polyethers from the Marine Red Alga Laurentia obtusa (Hudson) Lamouroux
Suzuki, Teruaki,Takeda, Satoshi,Suzuki, Minoru,Kurosawa, Etsuro,Kato, Arata,Imanaka, Yoshihiko
, p. 361 - 364 (2007/10/02)
Five new cytotoxic triterpenoids with squalene carbon skeleton have been isolated from the title alga.The structures of 15(18)-anhydrothyrsiferyl diacetate, 15-anhydrothyrsiferyl diacetate, and magireol-A were confirmed by the spectral and chemical methods.The structures of magireol-B and -C were deduced from spectral data.
Teurilene and thyrsiferyl 23-acetate, meso and remarkably cytotoxic compounds from the marine red alga Laurencia obtusa (Hudson) Lamouroux
Suzuki,Suzuki,Furusaki,et al.
, p. 1329 - 1332 (2007/10/02)
Two new cyclic ethers consisting of a squalene carbon skeleton have been isolated from the red alga L. obtusa. The absolute stereostructure of teurilene was elucidated by the X-ray crystallographic method, and the structure of thyrsiferyl 23-acetate was established from spectral and chemical evidence.
TERPENOIDS OF THE RED ALGA LAURENCIA PINNATIFIDA
Gonzalez, A. G.,Arteaga, J. M.,Fernandez, J. J.,Martin, J. D.,Norte, M.,Ruano, J. Z.
, p. 2751 - 2756 (2007/10/02)
The structures of three brominated terpenoids which are natural products from the red alga Laurencia pinnatifida (Gmal.Lamour) are described.The structures of the sesquiterpenes 4 and 5 were determined by spectral comparison and chemical interconversion.The structure of the squalene-derived terpenoid 8 was secured by chemical transformation into thyrsiferol, a brominated triterpene previously isolated from the red alga Laurencia thyrsifera.
