• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】50731

【品名】8-(tert-butoxy)-4a,7,8,8a-tetrahydro-1,4,6(5H)-naphthalenetrione

【CA登记号】

【 分 子 式 】C14H18O4

【 分 子 量 】250.29452

【元素组成】C 67.18% H 7.25% O 25.57%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IX)

The Diels-Alder cyclization of butadiene (VII) with 1,4-benzoquinone (VIII) in THF gives the naphthalenetrione (IX), which is acylated with acetic anhydride and TEA to yield the tetralone derivative (X). The Grignard reaction of (X) with vinylmagnesium bromide (XI) and CeCl3, followed by acylation with acetic anhydride, affords the tetraline derivative (XII), which is treated with NaBH4 and oxidized with cerium ammonium nitrate to provide the tetrahydronaphthoquinone (XIII). The cyclization of (XIII) with 4-acetoxy-3,4-dihydro-1H-2-benzopyran-1,3-dione (XIV) by means of NaH in THF gives the intermediate (XV), which rearranges to the tetracyclic dione (XVI). The palladium-catalyzed (PdCl2(MeCN)2) rearrangement of (XVI) in toluene yields the allyl acetate derivative (XVII), which is oxidized with peracetic acid and RuCl3 in water/acetonitrile/dichloromethane to afford the protected intermediate (XVIII). Finally, this compound is deprotected and simultaneously epimerized by a treatment with HCl in refluxing isopropanol/water to provide the desired target intermediate (II).

1 Hottop, T.; et al.; Synthesis of 4-demethoxyadriamycinone utilizing ruthenium-catalyzed oxidation of allyl acetates. Tetrahedron Lett 2001, 42, 19, 3343.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 50740 (7S,9S)-9-glycoloyl-6,7,9,11-tetrahydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione C20H16O8 详情 详情
(VII) 50730 [[(E)-3-(tert-butoxy)-1-methylene-2-propenyl]oxy](trimethyl)silane; (E)-3-(tert-butoxy)-1-methylene-2-propenyl trimethylsilyl ether C11H22O2Si 详情 详情
(VIII) 12633 Quinone; Benzo-1,4-quinone; 2,5-Cyclohexadiene-1,4-dione 106-51-4 C6H4O2 详情 详情
(IX) 50731 8-(tert-butoxy)-4a,7,8,8a-tetrahydro-1,4,6(5H)-naphthalenetrione C14H18O4 详情 详情
(X) 50732 4-(acetoxy)-5-(tert-butoxy)-7-oxo-5,6,7,8-tetrahydro-1-naphthalenyl acetate C18H22O6 详情 详情
(XI) 16524 bromo(vinyl)magnesium 1826-67-1 C2H3BrMg 详情 详情
(XII) 50733 (2S,4S)-5,8-bis(acetoxy)-4-(tert-butoxy)-2-vinyl-1,2,3,4-tetrahydro-2-naphthalenyl acetate C22H28O7 详情 详情
(XIII) 50734 (2S,4S)-4-(tert-butoxy)-5,8-dioxo-2-vinyl-1,2,3,4,5,8-hexahydro-2-naphthalenyl acetate C18H22O5 详情 详情
(XIV) 50735 1,3-dioxo-3,4-dihydro-1H-isochromen-4-yl acetate C11H8O5 详情 详情
(XV) 50736 (2S,4S)-6-(acetoxy)-4-(tert-butoxy)-11-hydroxy-5,12-dioxo-2-vinyl-1,2,3,4,5,12-hexahydro-2-naphthacenyl acetate C28H28O8 详情 详情
(XVI) 50737 (2S,4S)-2-(acetoxy)-4-(tert-butoxy)-12-hydroxy-6,11-dioxo-2-vinyl-1,2,3,4,6,11-hexahydro-5-naphthacenyl acetate C28H28O8 详情 详情
(XVII) 50738 2-[5-(acetoxy)-4-(tert-butoxy)-12-hydroxy-6,11-dioxo-3,4,6,11-tetrahydro-2(1H)-naphthacenylidene]ethyl acetate C28H28O8 详情 详情
(XVIII) 50739 (2S,4R)-2-[2-(acetoxy)acetyl]-4-(tert-butoxy)-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-5-naphthacenyl acetate C28H28O10 详情 详情
Extended Information