Journal
TETRAHEDRON
Volume 66, Issue 26, Pages 4687-4695Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.02.050
Keywords
Indoline; Natural products; Fischer indole synthesis; Total synthesis; Heterocycles
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Funding
- NIH-NIGMS [R00 GM079922]
- University of California, Los Angeles
- Boehringer Ingelheim
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A convergent method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. The method is convergent, mild, operationally simple, broad in scope, and can be used to access enantioenriched products. In addition, our approach is amenable to the synthesis of furoindoline and pyrrolidinoindoline natural products as demonstrated by the concise formal total syntheses of physovenine and debromoflustramine B. The strategy will likely enable the synthesis of more complex targets such as the communesin alkaloids. Published by Elsevier Ltd.
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