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Extra resources for A textbook of inorganic chemistry vol.XI part I Organometalic compounds. Derivatives of the elements of groups I to IV
Cyclization of 82 under Heck conditions yields the expected 7,8-dioxoerythrinane 83 as a single diastereomer, which then has been converted to (Æ)-2-epi-erythrinitol (84) in twelve additional steps (64). 28 E. Reimann Scheme 10. 2% (64) A new diastereoselective route to aromatic cis-erythrinanes represents the combined intramolecular Strecker and Bruylants reactions of the phenethyl-cyclohexanylethylamines 88 (Scheme 11). Deprotection of the carbonyl function and addition of potassium cyanide causes the Strecker reaction to give the angularly substituted hydroindole derivatives 89 in nearly quantitative yields.
1. Cyclization of Secondary Diphenethylor (Cycloalkyl)ethyl-phenethylamine Derivatives (Route B/C(a)) The ﬁrst syntheses of the erythrinane framework reported by Belleau (81, 82) and Mondon (83–86) have been performed using cyclization of the isomeric ketalamides 151 with polyphosphoric acid via the assumed Scheme 23. Synthesis of 8- and 10-oxoerythrinanes (68, 96, 153) (83–86): a) P4O10/PPA or PPA in varying concentrations, 20 to 100 C 40 E. Reimann Scheme 24. Synthesis of (Æ)-erysodienone (39) (87, 88): a) K3[Fe(CN)6]/Na2CO3 in H2O/CH2Cl2 intermediate N-acyliminium ion (152) giving the oxoerythrinanes 68, 96, and 153 (Scheme 23).
Reimann Scheme 38. Synthesis of (Æ)-3,17-demethoxy-1,2-dihydrocomosidine (210) (28): a) methyl acrylate in CHCl3/50 C; c, d, e: reagents are the same as in Scheme 14 Furthermore, the formation of the C ring can be also accomplished following the Friedel-Crafts method already indicated in the erythrinane series (Scheme 14). Accordingly, the cis-arylhydroindole 208 has been alkylated with methyl acrylate providing the N-substituted precursor 209 in excellent yield, which after cyclization and consecutive removal of the carbonyl group affords the (Æ)-3,17-demethoxy-1,2-dihydrocomosidine 210 (Scheme 38).
A textbook of inorganic chemistry vol.XI part I Organometalic compounds. Derivatives of the elements of groups I to IV