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General strategy for the synthesis of B-1 phytoprostanes, dinor isoprostanes, and analogs

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Schmidt,  A.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;
IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society;

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Boland,  W.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;

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Citation

Schmidt, A., & Boland, W. (2007). General strategy for the synthesis of B-1 phytoprostanes, dinor isoprostanes, and analogs. Journal of Organic Chemistry, 72(5), 1699-1706. doi:10.1021/jo062359x.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0012-A328-4
Abstract
The synthesis of the phytoprostane B-1 types I and II is achieved in high overall yield (35-53%) by only two principal transformations starting from 1,3-cyclopentanedione. The first side chain is attached via O-acylation of the 1,3-dione followed by rea