Total synthesis of complestatin: development of a Pd(0)-mediated indole annulation for macrocyclization.

ABSTRACT: Full details of the initial development and continued examination of a powerful intramolecular palladium(0)-mediated indole annulation for macrocyclization closure of the strained 16-membered biaryl ring system found in complestatin (1, chloropeptin II) and the definition of factors impacting its intrinsic atropodiastereoselectivity are described. Its examination and use in an alternative, second-generation total synthesis of complestatin are detailed in which the order of the macrocyclization reactions was reversed from our first-generation total synthesis. In this approach and with the ABCD biaryl ether ring system in place, the key Larock cyclization was conducted with substrate 36 (containing four phenols, five secondary amides, one carbamate, and four labile aryl chlorides) and provid

SUBMITTER: Shimamura H 

PROVIDER: S-EPMC2892899 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature