714974-01-3Relevant articles and documents
Synthesis of complex intermediates for the study of a dehydratase from borrelidin biosynthesis
Hahn, Frank,Kandziora, Nadine,Friedrich, Steffen,Leadlay, Peter F.
, p. 634 - 640 (2014/04/17)
Herein, we describe the syntheses of a complex biosynthesis-intermediate analogue of the potent antitumor polyketide borrelidin and of reference molecules to determine the stereoselectivity of the dehydratase of borrelidin polyketide synthase module 3. Th
Total synthesis of borrelidin
Nagamitsu, Tohru,Takano, Daisuke,Marumoto, Kaori,Fukuda, Takeo,Furuya, Kentaro,Otoguro, Kazuhiko,Takeda, Kazuyoshi,Kuwajima, Isao,Harigaya, Yoshihiro,Omura, Satoshi
, p. 2744 - 2756 (2008/02/05)
(Chemical Equation Presented) The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2·Et2O-mediated chelation-controlled allylation.