- Total synthesis of borrelidin.
Total synthesis of borrelidin.
The Journal of organic chemistry (2007-03-16)
Tohru Nagamitsu, Daisuke Takano, Kaori Marumoto, Takeo Fukuda, Kentaro Furuya, Kazuhiko Otoguro, Kazuyoshi Takeda, Isao Kuwajima, Yoshihiro Harigaya, Satoshi Omura
PMID17355148
ABSTRACT
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.