123438-47-1Relevant articles and documents
Synthesis, antitubulin, and antiproliferative sar of c3/c1-substituted tetrahydroisoquinolines
Dohle, Wolfgang,Leese, Mathew P.,Jourdan, Fabrice L.,Major, Meriel R.,Bai, Ruoli,Hamel, Ernest,Ferrandis, Eric,Kasprzyk, Philip G.,Fiore, Ann,Newman, Simon P.,Purohit, Atul,Potter, Barry V. L.
, p. 350 - 370 (2014/04/03)
The syntheses and antiproliferative activities of novel substituted tetrahydroisoquinoline derivatives and their sulfamates are discussed. Biasing of conformational populations through substitution on the tetrahydroisoquinoline core at C1 and C3 has a pro
Quinolizidines. VIII. Structure and Synthesis of the Alangium Alkaloid Alangicine: Syntheses of (+/-)- and (+)-Alangicines
Fujii, Tozo,Yamada, Koichiro,Minami, Shinzaburo,Yoshifuji, Shigeyuki,Ohba, Masashi
, p. 2583 - 2592 (2007/10/02)
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