Premium
Diastereo‐ and Enantioselective Total Synthesis of Stigmatellin A
Author(s) -
Enders Dieter,
Geibel Gunter,
Osborne Simon
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000417)6:8<1302::aid-chem1302>3.0.co;2-j
Subject(s) - aldol reaction , chemistry , enantioselective synthesis , stereochemistry , alkylation , total synthesis , aldol condensation , organic chemistry , catalysis
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 ) CC double bond formation via Horner‐Wadsworth‐Emmons reaction.