Part I, The total synthesis of (±)-securinine and (±)-allosecurinine and synthetic strategies for a second generation synthesis of the securinega alkaloids and Part II, The use of (+)-K252a in the semi-synthesis of indolocarbazole natural products and novel analogs thereof
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In part I, the total syntheses of (±)-securinine ((±)-1.001) and (±)-allosecurinine ((±)-1.003) are described. The syntheses feature the use of a Rh-initiated O—H insertion/Claisen rearrangement/1,2-allyl migration, which would allow for an enantioselective synthesis when an enantioenriched allylic alcohol (ie: (+)-1.137) is used. Three more steps generates the common intermediate imine 1.144, which upon reduction gives a pair of diastereomers. Protection of the free amine and a second reduction gives 1.146a and 1.146b, which were advanced to (±)-1.003 and (±)-1.001 respectively. Additional ...