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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Total synthesis and isolation of citrinalin and cyclopiamine congeners

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Author(s):
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Mercado-Marin, Eduardo V. [1] ; Garcia-Reynaga, Pablo [1] ; Romminger, Stelamar [2] ; Pimenta, Eli F. [2] ; Romney, David K. [3] ; Lodewyk, Michael W. [4] ; Williams, David E. [5] ; Andersen, Raymond J. [5] ; Miller, Scott J. [3] ; Tantillo, Dean J. [4] ; Berlinck, Roberto G. S. [2] ; Sarpong, Richmond [1]
Total Authors: 12
Affiliation:
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 - USA
[2] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
[3] Yale Univ, Dept Chem, New Haven, CT 06520 - USA
[4] Univ Calif Davis, Dept Chem, Davis, CA 95616 - USA
[5] Univ British Columbia, Dept Chem & Earth & Ocean Sci, Vancouver, BC V6T 1Z1 - Canada
Total Affiliations: 5
Document type: Journal article
Source: Nature; v. 509, n. 7500, p. 318-324, MAY 15 2014.
Web of Science Citations: 73
Abstract

Many natural products that contain basic nitrogen atoms-for example alkaloids like morphine and quinine-have the potential to treat a broad range of human diseases. However, the presence of a nitrogen atom in a target molecule can complicate its chemical synthesis because of the basicity of nitrogen atoms and their susceptibility to oxidation. Obtaining such compounds by chemical synthesis can be further complicated by the presence of multiple nitrogen atoms, but it can be done by the selective introduction and removal of functional groups that mitigate basicity. Here we use such a strategy to complete the chemical syntheses of citrinalin B and cyclopiamine B. The chemical connections that have been realized as a result of these syntheses, in addition to the isolation of both 17-hydroxycitrinalin B and citrinalin C (which contains a bicyclo{[}2.2.2]diazaoctane structural unit) through carbon-13 feeding studies, support the existence of a common bicyclo{[}2.2.2]diazaoctane-containing biogenetic precursor to these compounds, as has been proposed previously. (AU)

FAPESP's process: 12/50026-3 - International collaboration in the chemistry of alkaloid natural product biosynthesis
Grantee:Roberto Gomes de Souza Berlinck
Support type: Regular Research Grants