108344-52-1Relevant articles and documents
Synthesis of Bufalitoxin and Bufotoxin
Pettit, George R.,Kamano, Yoshiaki,Drasar, Pavel,Inoue, Masuo,Knight, John C.
, p. 3573 - 3578 (2007/10/02)
Completion of a formal total synthetic route to the toad venom constituents bufotalin (8), cinobufagin (2a), bufalitoxin (3f), and bufotoxin (1a) has been accomplished.Bufalin (3a) was employed as relay and converted to 14-dehydrobufalin 3-acetate (4).Selective oxidation of olefin 4 with a chromium trioxide-pyridine reagent afforded 16-ketone 5, which we had previously transformed to bufotalin (8) and thence to cinobufagin (2a).Condensation of bufalin (3a) with suberic anhydride followed by a mixed carbonic anhydride reaction sequence using arginine monohydrochloride yielded bufalitoxin (3f), and an analogous route from bufotalin (8) led to bufotoxin (1a).