Tandem photocycloaddition-retro-mannich fragmentation of enaminones. A route to spiropyrrolines and the tetracyclic core of koumine |
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Authors: | White James D Ihle David C |
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Affiliation: | Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA. james.white@oregonstate.edu |
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Abstract: | [reaction: see text] Intramolecular [2 + 2] photocycloaddition of beta-aminoalkylidene malonates gives transiently a cyclobutane which undergoes retro-Mannich fragmentation to a Delta(1)-pyrroline. The tandem sequence, exemplified in two series based on tryptamine and aminoethyl-1,4-cyclohexadiene, leads to a spiroindolopyrroline skeleton and to the nonindolenine portion of koumine. |
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