title: Total synthesis of cribrostatin IV: fine-tuning the character of an amide bond by remote control.
abstract: We report the enantioselective total synthesis of cribrostatin IV (1). Key features of this synthesis involve the convergent coupling of two highly functionalized homochiral components followed by a "lynchpin" Mannich cyclization to establish the pentacyclic core (cf. 19 --> 20).
authors.affiliation: Department of Chemistry, Columbia University, Havemeyer Hall, New York, NY 10027, USA.
authors.forename: Collin
authors.initials: C
authors.lastname: Chan
authors.forename: Richard
authors.initials: R
authors.lastname: Heid
authors.forename: Shengping
authors.initials: S
authors.lastname: Zheng
authors.forename: Jinsong
authors.initials: J
authors.lastname: Guo
authors.forename: Bishan
authors.initials: B
authors.lastname: Zhou
authors.forename: Takeshi
authors.initials: T
authors.lastname: Furuuchi
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D007546:Isoquinolines / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry
chemical_list: D000577:Amides; D007546:Isoquinolines; C412688:cribrostatin 4