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药物详细合成路线

Name Besigomsin;Gomisin A;Schisandrol B;TJN-101
Chemical Name (6S-trans)-5,6,7,8-Tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethylbenzo[3,4]cycloocta[1,2-f][1,3]benzodiox-6-ol
      (+)-(6S,7S-R-biar)-5,6,7,8-Tetrahydro-1,2,3,12-tetramethoxy-6,7-dimethyl-10,11-methylenedioxy-6-dibenzo[a,c]cyclooctenol
CAS 58546-54-6
Related CAS
Formula C23H28O7
Structure
Formula Weight 416.47541
Stage III 期临床
Company Tsumura (Originator)
Activity/Mechanism Agents for Liver Fibrosis, GASTROINTESTINAL DRUGS, Hepatoprotectants, Liver and Biliary Tract Disorders, Treatment of
Syn. Route 1
Route 1
a total synthesis of gomisin a has been published:the asymetric hydrogenation of 2-(carboxymethyl)-3-[3-methoxy-4,5-(methylenedioxy)phenyl]-2(e)-propenoic acid methyl ester (i) gives the (s)-isomer of the saturated hemiester (ii), which by reduction with calcium borohydride is converted into the lactone (iii). the aldol condensation with 3,4,5-trimethoxybenzaldehyde (iv), followed by dehydration with acetic anhydride, affords the benzylidene-lactone (v). the biphenyl cyclization of (v) with ferric perchlorate in dichloromethane - trifluoroacetic acid yields the dibenzocyclooctene compound (vi) (and its regioisomer). the reduction of (vi) with dibutylaluminum hydride affords diol (vii), which is acetylated with acetic anhydride to the diacetate (viii). the reaction of (viii) with ammonium formate and paladium chloride-triphenylphosphine complex and then with naoh gives the exo-methylene derivative (ix), which is epoxidized with oso4 - methanesulfonyl chloride and nah to the epoxide (x). finally, this compound is deprotected and submitted to ring-opening with lialh4.
List of intermediates No.
2-bromo-1-(3-bromo-5-isoxazolyl)-1-ethanone (i)
2-bromo-1-(3-bromo-5-isoxazolyl)-1-ethanol (ii)
3-bromo-5-(2-oxiranyl)isoxazole (iii)
2-(4-chlorophenyl)acetonitrile (iv)
1-(4-chlorophenyl)cyclobutanecarbonitrile (v)
1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylideneamine bromomagnesium salt (vi)
1-[1-(4-chlorophenyl)cyclobutyl]-3-methyl-1-butanone (vii)
1-[1-(4-chlorophenyl)cyclobutyl]-3-methyl-1-butanamine; 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine (viii)
bromo(isobutyl)magnesium (ix)
(9r,11s,17r)-9-fluoro-17-glycoloyl-11,17-dihydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-3-one (x)
Reference 1:
    mitsuhashi, h.; wakamatsu, t.; mukaiyama, c.; tanaka, m.; synthesis and optically pure gomisin a and schizandrin: the first total synthesis of gomisin a and schizandrin having naturally occurring configurations. tetrahedron lett 1992, 33, 29, 4165.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名五味子醇甲;英文名Besigomsin;Gomisin A;Schisandrol B;TJN-101;CAS[58546-54-6]

 
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