By von Angerer S., et al. (eds.)
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Additional info for Houben-Weyl Methoden der organischen Chemie vol.E9d Hetarenes III, Part 4
Ring closure CH 3 OH, Ag 2 O k. SnCI 4 h. SOCL i. CHJVL g. HBr I. Pd-C of the keto group and ring closure led to 8-keto-8,9,10,ll-tetrahydro-10MBA, 174, and from it 10-MBA and 8,10-DMBA were synthesized (Bachmann and Chemerda, 1938). Starting from the condensation product of 3-acetylphenanthrene with diethyl succinate and treatment of the first formed half-ester with hydrobromic acid there was obtained 30 Chemistry the lactone 175. The lactone was reduced to y-(3-phenanthryl)valeric acid, 176, which was then cyclized to 177.
Ring closure of 150 with cold concentrated sulphuric acid followed by hydrolysis afforded the diacid, 151. Dieckmann cyclization of the ester of 151 with sodium in benzene led to 4-ketoScheme 2 X . Dieckmann Cyclization. CO(CK 2 ) 3 CO 2 C 2 H 5 + a_ BA 4-MBA a. KOtbu b. H^SC^, -IO°C ester, hydrolysis,-CO 2 c. KOH, HgO f. L i A I H 4 d. HCl g. Pd-C e. Na, C 6 H 6 on the dimethyl h. C H 3 M g I 26 Chemistry 1,2,3,4,5,6-hexahydroBA, 152, Scheme XX. Reaction of 152 with LiAlH4 followed by aromatization over Pd-C yielded BA.
4-MBA 3,4-DMBA 4-E-3-MBA JJ9 (R :02H COOH (R«H) (R«H) Ig4 a. Br(CH2)4Br, base d. A,Pd-C Jg7(R«H) (R«CH3) b. reduction to alcohol c. dehydration e. Clemmensen reduction f. A , Pt-C g. A in (C^H5)2OI Pd-C h. alkaline hydrolysis i. standard chain lengthening steps methyl a-(3,4,5,6,7,8-hexahydro-l-anthryl)acetate, 123, and methyl a(3,4,5,6,7,8-hexahydro-l-anthryl)propionate, 124, respectively, after dehydration of the first-formed hydroxyesters (Newman and Otsuka, 1958), Scheme XVII. After conversion to 125 and 126, conventional chain-lengthening steps produced 127 and 128.
Houben-Weyl Methoden der organischen Chemie vol.E9d Hetarenes III, Part 4 by von Angerer S., et al. (eds.)