title: Total synthesis of cortistatins A and J.
abstract: This paper describes the details of our synthetic studies on the marine steroidal alkaloids cortistatins A and J. The key features of our strategy include (i) an efficient Knoevenagel/electrocyclic strategy to couple the diketone and the CD-ring fragment, (ii) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octene B-ring system, (iii) a highly stereocontrolled installation of the isoquinoline unit, and (iv) a late-stage functionalization of the A-ring.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. s-yamashita@m.tohoku.ac.jp
authors.forename: Shuji
authors.initials: S
authors.lastname: Yamashita
authors.forename: Kentaro
authors.initials: K
authors.lastname: Iso
authors.forename: Kazuki
authors.initials: K
authors.lastname: Kitajima
authors.forename: Masafumi
authors.initials: M
authors.lastname: Himuro
authors.forename: Masahiro
authors.initials: M
authors.lastname: Hirama
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000627:therapeutic use; D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000627:therapeutic use; D000818:Animals; D059001:Aquatic Organisms / Q000737:chemistry; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000627:therapeutic use; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D007659:Ketones / Q000737:chemistry; D009389:Neovascularization, Pathologic / Q000188:drug therapy / Q000517:prevention & control; D018919:Neovascularization, Physiologic / Q000187:drug effects; D009479:Neuropeptides / Q000138:chemical synthesis* / Q000627:therapeutic use; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000627:therapeutic use; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000627:therapeutic use
chemical_list: D000470:Alkaloids; D020533:Angiogenesis Inhibitors; D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines; D007659:Ketones; D009479:Neuropeptides; D011083:Polycyclic Compounds; D013256:Steroids; C099323:cortistatin; C531521:cortistatin A; C545305:cortistatin J; C039109:isoquinoline