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【结 构 式】

【分子编号】35729

【品名】7,7-dimethyl-1-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-3,4,5,6,7,8-hexahydro-2(1H)-naphthalenone

【CA登记号】

【 分 子 式 】C28H44O

【 分 子 量 】396.65676

【元素组成】C 84.79% H 11.18% O 4.03%

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:(VIII)

The methylation of 7-methoxy-1-tetralone (I) with methyl iodide and potassium tert-butoxide in THF gives the 2,2-dimethyl derivative (II), which is reduced with NaBH4 and acetylated with acetyl chloride yielding the acetate (III). The reduction of (III) with diethylborohydride in TFA affords 7-methoxy-2,2-dimethyltetraline (IV), which is submitted to a Birch reduction with Li/NH3 in THF affording 2,2-dimethyl-7-methoxy-1,2,3,4,5,8-hexahydronaphthalene (V). The condensation of (V) with homofarnesyl iodide (VI) by means of BuLi in THF gives intermediate (VII), which is treated with 2-sulfanylethanol and TFA yielding the ketone (VIII). The reaction of (VIII) with KHMDS and Tf2N-Ph in THF affords the enol triflate (IX), which is selectively brominated with N-bromosuccinimide (NBS) in THF giving the bromohydrine (X). The epoxidation of (X) with K2CO3 in methanol, followed by methylation with Me2CuLi in THF yields the epoxide (XI), which is treated with SiF4 and TFA to afford the fluoroketone (XII). The stereocontroled reduction of the ketone group of (XII) with a chiral oxaazaborolidine (OABL) gives the chiral alcohol (XIII), which is epoxidized by means of sodium isopropoxide in isopropanol yielding the chiral epoxide (XIV).

1 Corey, E.J.; Lee, J.; Enantioselective total synthesis of oleanolic acid, erythrodiol, beta-amyrin, and other pentacyclic triterpenes from a common intermediate. J Am Chem Soc 1993, 115, 8873.
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) 21385 7-methoxy-3,4-dihydro-1(2H)-naphthalenone 6836-19-7 C11H12O2 详情 详情
(II) 35723 7-methoxy-2,2-dimethyl-3,4-dihydro-1(2H)-naphthalenone C13H16O2 详情 详情
(III) 35724 7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydro-1-naphthalenyl acetate C15H20O3 详情 详情
(IV) 35725 7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene; 7,7-dimethyl-5,6,7,8-tetrahydro-2-naphthalenyl methyl ether C13H18O 详情 详情
(V) 35726 7,7-dimethyl-1,4,5,6,7,8-hexahydro-2-naphthalenyl methyl ether; 7-methoxy-2,2-dimethyl-1,2,3,4,5,8-hexahydronaphthalene C13H20O 详情 详情
(VI) 35727 (6E,10E)-13-iodo-2,6,10-trimethyl-2,6,10-tridecatriene C16H27I 详情 详情
(VII) 35728 7-methoxy-2,2-dimethyl-8-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-1,2,3,4,5,8-hexahydronaphthalene; 7,7-dimethyl-1-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-1,4,5,6,7,8-hexahydro-2-naphthalenyl methyl ether C29H46O 详情 详情
(VIII) 35729 7,7-dimethyl-1-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-3,4,5,6,7,8-hexahydro-2(1H)-naphthalenone C28H44O 详情 详情
(IX) 35730 7,7-dimethyl-1-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-3,4,5,6,7,8-hexahydro-2-naphthalenyl trifluoromethanesulfonate C29H43F3O3S 详情 详情
(X) 35731 1-[(3E,7E)-11-bromo-12-hydroxy-4,8,12-trimethyl-3,7-tridecadienyl]-7,7-dimethyl-3,4,5,6,7,8-hexahydro-2-naphthalenyl trifluoromethanesulfonate C29H44BrF3O4S 详情 详情
(XI) 35732 3-[(3E,7E)-3,7-dimethyl-10-(2,7,7-trimethyl-3,4,5,6,7,8-hexahydro-1-naphthalenyl)-3,7-decadienyl]-2,2-dimethyloxirane C29H46O 详情 详情
(XII) 35733 (6E,10E)-2-fluoro-2,6,10-trimethyl-13-(2,7,7-trimethyl-3,4,5,6,7,8-hexahydro-1-naphthalenyl)-6,10-tridecadien-3-one C29H45FO 详情 详情
(XIII) 35734 (3S,6E,10E)-2-fluoro-2,6,10-trimethyl-13-(2,7,7-trimethyl-3,4,5,6,7,8-hexahydro-1-naphthalenyl)-6,10-tridecadien-3-ol C29H47FO 详情 详情
(XIV) 35735 (3S)-3-[(3E,7E)-3,7-dimethyl-10-(2,7,7-trimethyl-3,4,5,6,7,8-hexahydro-1-naphthalenyl)-3,7-decadienyl]-2,2-dimethyloxirane C29H46O 详情 详情
Extended Information