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September 1, 1991The Journal of Organic Chemistry

Development of an asymmetric approach to the 3,8-diazabicyclo3.2.1octane moiety of quinocarcin via intramolecular 1,3-dipolar cycloadditions of photochemically generated azomethine ylides

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Authors

PGPhilip GarnerWashington State UniversityWHWen Bin HoSGSunitha K. GrandheeCase Western Reserve University

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Overview

Chemical synthesis study demonstrates an asymmetric route to quinocarcin's core framework via photochemical cycloadditions, highlighting a strategy for constructing complex natural alkaloids.

Key Points

  • Develop an asymmetric synthetic pathway to construct the complex 3,8-diazabicyclo[3.2.1]octane core architecture of the antitumor antibiotic quinocarcin.
  • Generated reactive azomethine ylide intermediates through photochemical activation.
  • Conducted intramolecular 1,3-dipolar cycloadditions to forge the bridged bicyclic diazabicyclooctane skeleton with controlled stereochemistry.
  • Successfully established an asymmetric route toward the bicyclic ring core characteristic of quinocarcin alkaloids.
  • Demonstrated that light-activated intramolecular dipolar cycloadditions reliably construct the sterically demanding nitrogen-containing bridged bicyclic framework.

Cite This Study

Garner et al. (1991) studied this question.

synapsesocial.com/papers/6a8091e4e1341be402e4838bhttps://doi.org/10.1021/jo00020a035
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