175673-54-8Relevant academic research and scientific papers
Epoxidation of electron deficient alkenes using tert-butyl hydroperoxide and 1,5,7-triazabicyclo[4.4,0]dec-5-ene and its Derivatives
Genski, Thorsten,Macdonald, Gregor,Wei, Xudong,Lewis, Norman,Taylor, Richard J. K.
, p. 795 - 797 (1999)
The title cyclic guanidine (4a) is an efficient promoter of enone epoxidation by tert-butyl hydroperoxide. Optimisation studies are reported and the procedure applied to cyclic and acyclic ketones, quinones and naphthoquinones. N-Substituted guanidine (4c) proved best for the epoxidation of 2-amidobenzoquinones. Preliminary asymmetric epoxidation studies are also discussed.
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.
The synthesis of novel analogues of the manumycin family of antibiotics and the antitumour antibiotic LL-C10037α
Kapfer, Isabelle,Lewis, Norman J.,Macdonald, Gregor,Taylor, Richard J. K.
, p. 2101 - 2104 (2007/10/03)
Efficient approaches to the central amino-epoxycyclohexenone core of the manumycin family of antibiotics are described. The use of this methodology to prepare the antitumour antibiotic LL-C10037α and its epimer, both in racemic form, and a number of analogues of manumycin, alisamycin and asukamycin, lacking the C-4 substituent, are then outlined.
