935872-06-3Relevant articles and documents
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.