Synthesis of trans, trans, cis-fused tetracyclic skeleton via radical domino cyclization. Issue 16 (20th April 2017)

• Record Type: Journal Article
• Authors: Furuta, Miyu; Hanaya, Kengo; Sugai, Takeshi; Shoji, Mitsuru
• Is Part Of: Tetrahedron. Volume 73:Issue 16(2017)
• Page Start: 2316
• Page End: 2322
• Publication Date: 2017-04-20
• Subjects: Limonoid -- Tetracyclic core -- Domino cyclization -- Radical cyclization -- Stereoselective; SXSRCXGZFGBWLY-GNQVVUJNSA-N -- DLXDZUNBGBZSAS-ATTXQUAZSA-N -- IMEIIXNRVTZXEP-QXPFVDMISA-N -- YFGBRSLPYOXIHB-HAHDFKILSA-N -- IMGDWNRAABVFDS-RHANQZHGSA-N -- VCIPTOWPKMFXTE-VQNDASPWSA-N -- UPNREPKMKYTWFR-URAKCZSFSA-N -- LXPRDPVRRHMXNZ-RHANQZHGSA-N -- VBORUBVKWRXZGT-MTJSOVHGSA-N -- NNXWFLIHNLFCQO-URAKCZSFSA-N -- XLHPNPCRGDTXJC-ONUIUJJFSA-N -- RAZVPHLABUDPRU-UHFFFAOYSA-N -- TZJYDKFJRXLSMI-UHFFFAOYSA-N -- PDSLFTTZNPVOTE-LVUSMNHTSA-N -- YOVIGZUMVKSFEM-UHFFFAOYSA-N -- XLYDMNQEOHXHOL-KGIZISNOSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.03.021
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Limonoids are characterized by a polycyclic structure and show a wide variety of bioactivities. In particular, mesendanin L, 12-hydroxyamoorastatone, and meliatoosenin F have unique structures containing a trans -A/B/C and cis -C/D-fused tetracyclic skeleton. We synthesized the core structure of these limonoids via Mn(OAc)3 and Cu(OAc)2 -mediated radical domino cyclization of an acyclic tetraene precursor having a terminal β-keto ester. To the best of our knowledge, this is the first example of the radical-mediated construction of a 6/6/6/5-membered tetracyclic skeleton. Graphical abstract: