61194-41-0

Upstream product

• 56774-72-2 ethyl (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-acetate 
• 57130-35-5 (2R,3R,11bS)-(-)-8-(Benzyloxy)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-acetic Acid Ethyl Ester 

Downstream Products

• 61194-42-1 (+/-)-8-benzyloxy-N-(3-benzyloxy-4-methoxyphenethyl)-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2β-acetamide 
• 69437-62-3 (+/-)-8-benzyloxy-2β-<(4,9-dihydro-3H-pyrido<3,4b>indol-1-yl)methyl>-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine 
• 61194-42-1 (2R,3R,11bS)-(-)-8-benzyloxy-N-(3-benzyloxy-4-methoxyphenethyl)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzoquinolizine-2-acetamide 
• 13849-53-1 alangimarckine 
• 69437-62-3 (2R, 3R, 11bS)-(+)-8-benzyloxy-2-<(4,9-dihydro-3H-pyrido<3,4b>indol-1-yl)methyl>-3-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine 
• 69461-03-6 <2S-<2α(R^*),3β,11bβ>>-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-<(2,3,4,9-tetrahydro-1H-pyrido<3,4b>indol-1-yl)methyl>-2H-benzoquinolizine 
• 69461-02-5 <2S-<2α(S^*),3β,11bβ>>-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-<(2,3,4,9-tetrahydro-1H-pyrido<3,4b>indol-1-yl)methyl>-2H-benzoquinolizine 
• 16531-04-7 (2R,3R,11bS)-(+)-2-(3,4-dihydro-6-hydroxy-7-methoxy-1-isoquinolyl)methyl-3-ethyl-1,3,4,6,7,11b-hexahydro-8-hydroxy-9,10-dimethoxy-2H-benzoquinolizine (alangicine) 
• 69461-01-4 (2R, 3R, 11bS)-(+)-8-benzyloxy-3-ethyl-1,3,4,6,7,11b-hexahydro-N-<2-(indol-3-yl)ethyl>-9,10-dimethoxy-2H-benzoquinolizine-2-acetamide 
• 61194-43-2 (+/-)-8-benzyloxy-2β-(6-benzyloxy-3,4-dihydro-7-methoxy-1-isoquinolyl)methyl-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine 
• 88909-02-8 (+/-)-8-benzyloxy-2β-(3,4-dihydro-6-hydroxy-7-methoxy-1-isoquinolyl)methyl-3α-ethyl-1,3,4,6,7,11bα-hexahydro-9,10-dimethoxy-2H-benzoquinolizine 
• 16531-04-7 (+/-)-2β-(3,4-dihydro-6-hydroxy-7-methoxy-1-isoquinolyl)methyl-3α-ethyl-1,3,4,6,7,11bα-hexahydro-8-hydroxy-9,10-dimethoxy-2H-benzoquinolizine<(+/-)-alangicine> 
• 65891-86-3 (+/-)-8-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-N-<2-(indol-3-yl)ethyl>-9,10-dimethoxy-2H-benzoquinolizine-2β-acetamide 

Relevant academic research and scientific papers

Quinolizidines. VIII. Structure and Synthesis of the Alangium Alkaloid Alangicine: Syntheses of (+/-)- and (+)-Alangicines

The first total synthesis of alangicine (3), an Alangium lamarckii alkaloid, has been achieved in the form of a racemic modification by means of an initial alkaline hydrolysis of the (+/-)-tricyclic ester 6 and succeeding steps proceeding through the intermediates (+/-)-7, (+/-)-10, and (+/-)-9.A parallel synthetic route starting with the (-)-tricyclic ester 6, derived from (+)-cincholoipon ethyl ester (8), produced the chiral target molecule (+)-3 via the intermediates (-)-7, (-)-10, and 9.The identity of the synthetic (+)-3 with alangicine unequivocally established the structure and absolute stereochemistry of this alkaloid.The (13)C nuclear magnetic resonance spectra of (+/-)-alangicine (3) and the ipecac and Alangium alkaloid psychotrine (18) confirmed their endocyclic double bond structures in the dihydroisoquinoline moiety.Catalytic reductions of 11, (+/-)-12, and 15 using hydrogen and Pd-C were investigated, and the results have shown that hydrogenolysis of the benzyloxy group proceeds much faster than saturation of the endocyclic C=N bond.Keywords - alangicine; psychotrine; structure; absolute configuration; stereoselective synthesis; (13)C NMR; CD; benzyl ether; hydrogenolysis