208706-21-2Relevant academic research and scientific papers
The synthesis of alisamycin, nisamycin, LL-C10037α and novel epoxyquinol and epoxyquinone analogues of manumycin A
Taylor, Richard J. K.,Alcaraz, Lilian,Kapfer-Eyer, Isabelle,Macdonald, Gregor,Wei, Xudong,Lewis, Norman
, p. 775 - 790 (2007/10/03)
Versatile synthetic routes are described for the preparation of a range of epoxyquinol and epoxyquinone analogues of the antitumour antibiotic manumycin A lacking the lower side chain, and these procedures have also been applied to prepare the bioactive natural product LL-C10037α. The extension of this methodology to provide a general synthetic route to the manumycin family of antibiotics is discussed and exemplified by the first total synthesis of alisamycin and ent-alisamycin. This route includes the novel, stereoselective organometallic addition of the Corey-Wollenberg reagent (E- 2-tributylstannylethenyllithium) to the manumycin nucleus and palladium catalysed Stille coupling technology for the introduction of the polyunsaturated 2-amino-3-hydroxycyclopentenone derived amide. Similar methodology has also been employed to complete the first total synthesis of the antibiotic nisamycin.
