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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Diastereo- and enantioselective total synthesis of stigmatellin A.

Stigmatellin A (1) isolated from the myxobacterium Stigmatella aurantiaca is a powerful inhibitor of electron transport in mitochondria and chloroplasts. The first highly diastereo- and enantioselective total synthesis of this important natural product is described. Key steps in the synthesis are the alkylation of the SAMP-hydrazone (S)-13, a titanium mediated syn-diastereoselective aldol reaction, the anti-diastereoselective triacetoxyborohydride reduction of the aldol adduct (R,R,S)-16, formation of the chromone system via Baker Venkataraman rearrangement and exclusive (E) C=C double bond formation via Horner-Wadsworth-Emmons reaction.[1]

References

  1. Diastereo- and enantioselective total synthesis of stigmatellin A. Enders, D., Geibel, G., Osborne, S. Chemistry (Weinheim an der Bergstrasse, Germany) (2000) [Pubmed]
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