Abstract |
The first total syntheses of welwitindolinone A and the most complex members of the fischerindole family, fischerindoles I and G, are reported. Highlights of these short, protecting-group-free syntheses include the application of the recently developed direct indole-carbonyl coupling, a simple approach for installing the quaternary center with neighboring chlorine atom, a regioselective dehydrogenation/ dehydration cascade to access fischerindole I, and a remarkably facile oxidative ring contraction to construct welwitindolinone A. An alternative biogenetic hypothesis, whose accuracy is suggested by the success of the current syntheses, is also put forth for this alkaloid family.
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Authors | Phil S Baran, Jeremy M Richter |
Journal | Journal of the American Chemical Society
(J Am Chem Soc)
Vol. 127
Issue 44
Pg. 15394-6
(Nov 09 2005)
ISSN: 0002-7863 [Print] United States |
PMID | 16262402
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)
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Chemical References |
- Alkaloids
- Indole Alkaloids
- Indoles
- Nitriles
- fischerindole
- welwitindolinone A
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Topics |
- Alkaloids
(chemical synthesis, chemistry)
- Cyanobacteria
(chemistry)
- Indole Alkaloids
- Indoles
(chemical synthesis, chemistry)
- Molecular Structure
- Nitriles
(chemical synthesis, chemistry)
- Stereoisomerism
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