Radicalinifated tandem bicyclizafon process 2

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Unformatted text preview: 1996 7 Retrosynthetic Analysis and Strategy of hisutene H H H 5-exo-dig H 1: hirustene H Intermolecular hydrogen transfer radical cyclization H H H 131 132 Transitory tricyclic vinyl radical 5-exo-trig radical cyclization H bicyclic ter7ary radical M THPO I 135 + H 136 H C-C bond formation H H 134 Nicolaou, Classics in Total Synthesis, 1996 H Monocyclic Primary radical 133 8 Retrosynthetic Analysis and Strategy of hirsutene •  4 conFguous stereogenic centers H * –  1 is quaternary * H * * •  Primary Iodide, 134, transformed directly to hirustene H 1.  Radical ­iniFated tandem bicyclizaFon process 2.  TerminaFng hydrogen atom transfer I H 1.) radical cyclization 2.) terminating H H H trans ­disubsFtuted 134 cyclopentene H 1: hirustene H –  2 C ­C...
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