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.
Enders
D
D
Institut für Organische Chemie der Technischen Hochschule, Aachen, Germany. enders@RWTH-aachen.de
Geibel
G
G
Osborne
S
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry; D013057:Spectrum Analysis; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D011090:Polyenes; C041573:stigmatellin