Open AccessConfiguration of the C(20) Epimer of 7,8-Dihydrobatrachotoxinin A
Author(s) -
Isabella L. Karle
Publication year - 1972
Publication title -
proceedings of the national academy of sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.69.10.2932
Subject(s) - epimer , molecule , ring (chemistry) , chemistry , stereochemistry , crystallography , batrachotoxin , ether , sodium , organic chemistry , sodium channel
7,8-Dihydrobatrachotoxinin A is an intermediate in the synthesis of batrachotoxin, the extremely potent venom from the Colombian frog Phyllobates aurotaenia. A crystal structure analysis by x-ray diffraction has confirmed that the intermediate is identical with the natural batrachotoxinin A except for the saturation of the C(7)-C(8) bond. There are seven asymmetric carbon atoms in the molecule. The cis A/B and C/D ring junctions cause the molecule to assume the characteristic shape of cardioactive steroids. A cage is formed from the A-ring, atom C(9), and the O atom that makes the ether linkage between C(3) and C(9).
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