Ontology highlight
ABSTRACT:
SUBMITTER: Navarro R
PROVIDER: S-EPMC3445413 | biostudies-literature | 2012 Sep
REPOSITORIES: biostudies-literature
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]