251556-92-0Relevant articles and documents
Stereocontrolled preparation of the C1-C14 polyene fragment of benzenic ansamycin antibiotics ansatrienin A and B
Sch?ning, Kai-Uwe,Wittenberg, Rüdiger,Kirschning, Andreas
, p. 1624 - 1626 (1999)
A practical synthesis of the C1-C14 polyene unit 5 in ansatrienin A (mycotrien l), 1a, and other ansamycin antibiotics is described which involves elaboration of the chiral unsaturated aldehyde 6 and phosphonate 7, followed by coupling of the building blocks by Horner-Emmons-olefination and Duthaler's aldolation. The synthesis of 6 successfully applies two consecutive Evans-aldol reactions for constructing the carbon backbone.