title: Diastereo- and enantioselective total synthesis of stigmatellin A.
abstract: 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.
authors.affiliation: Institut für Organische Chemie der Technischen Hochschule, Aachen, Germany. enders@RWTH-aachen.de
authors.forename: D
authors.initials: D
authors.lastname: Enders
authors.forename: G
authors.initials: G
authors.lastname: Geibel
authors.forename: S
authors.initials: S
authors.lastname: Osborne
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry; D013057:Spectrum Analysis; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D011090:Polyenes; C041573:stigmatellin