Total synthesis of (-)-kendomycin.
An enantioselective synthesis of (-)-kendomycin is described and is based on the application of the organosilane-based [4 + 2]-annulation strategy for the assembly of the C1a-C10 fragment. An underutilized samarium(II) iodide-assisted cyclization (intramolecular Barbier-type reaction) is employed to afford the protected macrocycle.
Lowe
Jason T
JT
Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek
James S
JS
D003500:Cyclization; D007454:Iodides / Q000737:chemistry; D017828:Rifabutin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012493:Samarium / Q000737:chemistry; D013237:Stereoisomerism
D007454:Iodides; C485395:kendomycin; D017828:Rifabutin; D012493:Samarium; C409809:samarium diiodide