Literature DB >> 4507615

Configuration of the C(20) epimer of 7,8-dihydrobatrachotoxinin A.

I L Karle.   

Abstract

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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Year:  1972        PMID： 4507615      PMCID： PMC389677          DOI： 10.1073/pnas.69.10.2932

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  7 in total

1.  Batrachotoxin: chemistry and pharmacology.

Authors:  E X Albuquerque; J W Daly; B Witkop
Journal:  Science       Date:  1971-06-04       Impact factor: 47.728

2.  [Steroids and sex hormones. 241. The partial synthesis of 3-methoxy--3-, 9- -oxido-7- hydroxy-11- -acetoxy-5- steroids].

Authors:  R Imhof; F E Gössinger; W Graf; W Schnüriger; H Wehrli
Journal:  Helv Chim Acta       Date:  1971       Impact factor: 2.164

3.  The structure of batrachotoxinin A, a novel steroidal alkaloid from the Colombian arrow poison frog, Phyllobates aurotaenia.

Authors:  T Tokuyama; J Daly; B Witkop; I L Karle; J Karle
Journal:  J Am Chem Soc       Date:  1968-03-27       Impact factor: 15.419

4.  The structure of batrachotoxin, a steroidal alkaloid from the Colombian arrow poison frog, Phyllobates aurotaenia, and partial synthesis of batrachotoxin and its analogs and homologs.

Authors:  T Tokuyama; J Daly; B Witkop
Journal:  J Am Chem Soc       Date:  1969-07-02       Impact factor: 15.419

5.  The crystal structure of digitoxigenin, C23H34O4.

Authors:  I L Karle; J Karle
Journal:  Acta Crystallogr B       Date:  1969-03-15       Impact factor: 2.266

6.  The structural formula and crystal structure of the O-p-bromobenzoate derivative of batrachotoxinin A, C31H38NO6Br, a frog venom and steroidal alkaloid.

Authors:  I I Karle; J Karle
Journal:  Acta Crystallogr B       Date:  1969-03-15       Impact factor: 2.266

7.  [Steroids and sex hormones. 242. Preparation of 14-beta-hydroxy-2-keto-delta-16-steroids: a new highly productive access to 33-O-methyl-17-alpha, 20-xi-tetrahydrobatrachotoxinin A].

Authors:  E Gössinger; W Graf; R Imhof; H Wehrli
Journal:  Helv Chim Acta       Date:  1971       Impact factor: 2.164
  7 in total

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