Hirustne h h 2 912capnellene triquinone or

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Unformatted text preview: chemo ­, regio ­, and stereo ­ selecFvity because of mild reacFon condiFons 5 Tandem Radical Cyclization •  Creates cyclic structures –  Very fast –  Favors 5 ­membered ring synthesis 5 ­exo ­trig 6 ­endo ­trig or X homolytic cleavage  –  dig  •  Sp –  Trig •  Sp2 –  Tet Y  •  sp3 Nicolaou, Classics in Total Synthesis, 1996 6 Hirsutene •  Hirsutene and Δ ­capnellene isomers H HH H 1: hirustne H H 2: Δ9(12) ­capnellene •  Triquinone or tricyclopentanoid natural product H •  3 classes H •  Linear H Hirustene H •  Angular (a linear triquinane) •  Propellane H pentalenene (an angular triquinane) modhephene (a propallane) •  Posses anFobioFc and/or anFtumor acFvity •  Curran’s tandem radical cyclizaFon can form more than one ring in a single step. Nicolaou, Classics in Total Synthesis,...
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This document was uploaded on 03/01/2014 for the course CEM 852 at Michigan State University.

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