Helioxanthin, ACH-126447
10-(1,3-苯并二氧戊环-5-基)呋喃并[3',4':6,7]萘并[1,2-d]-1,3-二氧杂环戊烯-7(9H)-酮Chemical Name: 10-(1,3-Benzodioxol-5-yl)furo[3',4':6,7]naphtho[1,2-d]-1,3-dioxol-7(9H)-one
CAS No. 18920-47-3
项目整合开发状态: Preclinical
项目研究机构: Yale University (Originator), Achillion (Licensee)
合成路线:Alternatively,the condensation of 1,3-benzodioxole-5-carbaldehyde ethylene ketal (VIII) with carbaldehyde (V) by means of n-BuLi gives the hydroxy ketal (IX),which is treated with Ac2O,HOAc and maleic anhydride (XI) at 140 C to perform a Diels-Alder cyclization between the nonisolated isobenzofuran (X) (a reactive diene) and the maleic anhydride (the dienophile),giving rise to the cyclic anhydride (XII).Finally,this compound is reduced with NaBH4 to the target compound along with some structural isomer (XIII) that is separated by chromatography.
📌 参考资料/链接：
参考文献标题:Activity of a novel camptothecin analogue,homocamptothecin,in camptothecin-resistant cell lines with topoisomerase I alterations
文献作者:Urasaki,Y.; Takebayashi,Y.; Pommier,Y.
参考来源:Cancer Res 2000,60(23),6577
📄 详细内容
合成路线:The condensation of 4-iodo-1,3-benzodioxole-5-carbaldehyde (I) with dimethyl succinate (II) by means of NaOMe in aqueous methanol gives the benzylidene derivative (III),which is condensed with 1,3-benzodioxole-5-carbaldehyde (IV) by means of NaOMe in methanol,affording the bis-benzylidene hemiester (V).The selective reduction of (V) with LiEt3BH,followed by lactonization with ethyl chloroformate and TEA in THF,yields the lactone (VI),which is finally cyclized by means of Pd(OAc)2 and K2CO3 at 110 C through the nonisolated intermediate (VII),providing the target compound.
参考文献标题:The first regiospecific synthesis of helioxanthin by novel palladium-catalyzed benzannulation reaction of alpha,beta-bisbenzylidene-gamma-lactone
文献作者:Mizufune,H.; et al.
参考来源:Tetrahedron Lett 2001,42(3),437
产品链接: CAS No. 18920-47-3››