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【结 构 式】

【分子编号】31517

【品名】(3S,4S)-7,9-dimethoxy-4-(methoxymethoxy)-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-10-ol

【CA登记号】

【 分 子 式 】C18H22O6

【 分 子 量 】334.36908

【元素组成】C 64.66% H 6.63% O 28.71%

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 title compound was originally isolated from the culture broths of Verticillum sp. The synthesis of this compound has been further described. The unsaturated lactone (I) was isomerized at the C-4 hydroxyl group, and subsequently protected as the methoxymethyl ether (II). Condensation of (II) with benzoate ester (III) in a tandem Michael addition-Dieckmann cyclization reaction afforded the tricyclic compound (IV), which was aromatized to the naphthopyranone (V) by treatment with cyclohexene and Pd/C. Protection of the hydroxyl group of (V) with benzyl bromide and K2CO3 gave benzyl ether (VI). After reduction of the lactone function of (VI) to the corresponding lactol by means of DIBAL, further deoxygenation with triethylsilane and trifluoroacetic acid provided the cyclic ether (VII). The benzyl group of (VII) was removed by hydrogenolysis with cyclohexadiene (VIII) and Pd/C, and the resulting hydroxynaphthopyran (IX) was oxidatively dimerized, affording (X) as a diasteromeric mixture. Aromatization of (X) by NaOH produced the bisnaphthol (XI).

1 Yamazaki, T.; Yoshimoto, T.; Tatsuta, K.; Synthesis and biological evaluation of the analogs of bioxanthracenes ES-242s, N-methyl-D-aspartate antagonists. J Antibiot 1998, 51, 3, 383.
2 Yamazaki, T.; Nagai, T.; Tamura, T.; Tatsuta, K.; Mase, T.; Synthesis of an N-methyl-D-aspartate receptor antagonist, ES-242-5, and its analogs. J Antibiot 1999, 52, 4, 422.
3 Nakamura, H.; Absolute and atropisomeric structure of ES-242s, N-methyl-D-aspartate receptor antagonists. J Antibiot 1999, 52, 4, 433.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 31509 (5R,6S)-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one C6H8O3 详情 详情
(II) 31510 (5S,6S)-5-(methoxymethoxy)-6-methyl-5,6-dihydro-2H-pyran-2-one C8H12O4 详情 详情
(III) 31511 methyl 2,4-dimethoxy-6-methylbenzoate 6110-37-8 C11H14O4 详情 详情
(IV) 31512 (3S,4S,4aR)-10-hydroxy-7,9-dimethoxy-4-(methoxymethoxy)-3-methyl-3,4,4a,5-tetrahydro-1H-benzo[g]isochromen-1-one C18H22O7 详情 详情
(V) 31513 (3S,4S)-10-hydroxy-7,9-dimethoxy-4-(methoxymethoxy)-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-1-one C18H20O7 详情 详情
(VI) 31514 (3S,4S)-10-(benzyloxy)-7,9-dimethoxy-4-(methoxymethoxy)-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-1-one C25H26O7 详情 详情
(VII) 31515 (3S,4S)-10-(benzyloxy)-7,9-dimethoxy-4-(methoxymethoxy)-3-methyl-3,4-dihydro-1H-benzo[g]isochromene; benzyl (3S,4S)-7,9-dimethoxy-4-(methoxymethoxy)-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-10-yl ether C25H28O6 详情 详情
(VIII) 31516 1,4-cyclohexadiene 628-41-1 C6H8 详情 详情
(IX) 31517 (3S,4S)-7,9-dimethoxy-4-(methoxymethoxy)-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-10-ol C18H22O6 详情 详情
(X) 31518 5,5'-Bis[7,9-dimethoxy-4(S)-(methoxymethoxy)-3(S)-methyl-3,4,5,10-tetrahydro-1H-naphtho[2,3-c]pyran-10-one] C36H42O12 详情 详情
(XI) 31519 5,5'-Bis[7,9-dimethoxy-4(S)-(methoxymethoxy)-3(S)-methyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-10-ol] C36H42O12 详情 详情
Extended Information