97743-96-9Relevant academic research and scientific papers
Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B
Lu, Xiao-Long,Qiu, Yuanyou,Yang, Baochao,He, Haibing,Gao, Shuanhu
, p. 4747 - 4752 (2021)
The asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B was achieved in 6-7 steps using an easily accessiblemeso-cyclohexadienone derivative. The [6,6]-bicyclic decalin B-C ring and the all-carbon quaternary stereocenter at C-6 were preparedviaa desymmetric intramolecular Michael reaction with up to 97% ee. The naphthalene diol D-E ring was constructed through a sequence of Ti(Oi-Pr)4-promoted photoenolization/Diels-Alder, dehydration, and aromatization reactions. This asymmetric strategy provides a scalable route to prepare target molecules and their derivatives for further biological studies.
Synthesis of biotinylated xestoquinone that retains inhibitory activity against Ca2+ ATPase of skeletal muscle myosin
Nakamura, Mitsuhiro,Kakuda, Takahiko,Oba, Yuichi,Ojika, Makoto,Nakamura, Hideshi
, p. 3077 - 3082 (2007/10/03)
Xestoquinone isolated from a marine sponge binds to skeletal muscle myosin and inhibits its Ca2+ ATPase activity. In this study, we first examined xestoquinone and its analogues to assess the relationships between structure and myosin Ca2+ ATPase inhibitory activity. On the basis of the resultant data, we then designed a biotinylated xestoquinone analogue. Xestoquinone and its analogues were derived from extracts of the marine sponge Xestospongia sapra. Four xestoquinone analogues with a quinone structure significantly inhibited Ca2+ ATPase activity. In contrast, four xestoquinone analogues in which the quinone structure was converted to a quinol dimethyl ether did not inhibit Ca2+ ATPase activity. This suggests that the quinone moiety is essential for inhibitory activity. Then, we synthesized a biotinylated xestoquinone in which a biotin tag was introduced to a site far from the quinone moiety, and this molecule exhibited stronger inhibitory activity than that of xestoquinone. This biotinylated xestoquinone could be useful as a probe in studies of the xestoquinone-myosin binding mode.
Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives
Sutherland, Hamish S,Higgs, Kerianne C,Taylor, Nicholas J,Rodrigo, Russell
, p. 309 - 317 (2007/10/03)
Syntheses of (±)-xestoquinone, (±)-9-methoxyxestoquinone and (±)-10-methoxyxestoquinone are described. A convergent CD plus ABE plan using the appropriate isobenzofuran (CD) and naphthofuranone (ABE) has been implemented to provide these marine metabolite
Silver salt effects on an asymmetric Heck reaction. Catalytic asymmetric total synthesis of (+)-xestoquinone
Miyazaki, Futoshi,Uotsu, Koichiro,Shibasaki, Masakatsu
, p. 13073 - 13078 (2007/10/03)
An enantioselective total synthesis of (+)-xestoquinone has been achieved using a cascade-type asymmetric Heck reaction (in up to 63% ee and 39% chemical yield (66% conversion yield)) of the aryl bromide derivative(4). The use of a larger amount of silver
Total synthesis of (+)-xestoquinone using an asymmetric palladium-catalyzed polyene cyclization
Maddaford, Shawn P.,Andersen, Neil G.,Cristofoli, Walter A.,Keay, Brian A.
, p. 10766 - 10773 (2007/10/03)
The first total asymmetric synthesis of (+)-xestoquinone (I) has been accomplished in 68% ee by a palladium(0)-catalyzed polyene cyclization of naphthyl triflate 44 using (S)-(+)-BINAP as the chiral ligand. Attempts at an asymmetric polyene cyclization using the corresponding naphthyl bromide 41 gave poor enantioselectivities even in the presence of silver salts, thus exemplifying the effect of the coordination state of palladium on the enantioselectivity. A new method for the preparation of 6,7-dihydroisobenzofurans is also described using a [1,2]-Wittig rearrangement on a seven-membered cyclic ether precursor.
