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Rapid construction of the aza-propellane core of acutumine via a photochemical [2 + 2] cycloaddition reaction.


ABSTRACT: Synthetic efforts toward the chlorinated aza-propellane alkaloid acutumine (1) are described. The key vicinal quaternary centers were constructed by a photochemical [2 + 2] cycloaddition reaction of a furanyl-tetrahydroindolone. Dihydroxylation of the [2 + 2] product enabled a tandem retro-aldol/intramolecular ketalization reaction, which revealed the aza-propellane core of 1 while generating an unusual, caged, pentacyclic hemiketal product.

SUBMITTER: Navarro R 

PROVIDER: S-EPMC3445413 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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Rapid construction of the aza-propellane core of acutumine via a photochemical [2 + 2] cycloaddition reaction.

Navarro Raul R   Reisman Sarah E SE  

Organic letters 20120814 17


Synthetic efforts toward the chlorinated aza-propellane alkaloid acutumine (1) are described. The key vicinal quaternary centers were constructed by a photochemical [2 + 2] cycloaddition reaction of a furanyl-tetrahydroindolone. Dihydroxylation of the [2 + 2] product enabled a tandem retro-aldol/intramolecular ketalization reaction, which revealed the aza-propellane core of 1 while generating an unusual, caged, pentacyclic hemiketal product. ...[more]

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