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June 5, 1996Journal of the American Chemical Society

Stereocontrolled Synthesis of (±)-12a-Deoxytetracycline

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Authors

GSGilbert StorkChemical Synthesis LabJCJames J. La ClairUniversity of California, San DiegoPSPeter L. SpargoEast Sussex County Council

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Implication

Laboratory study demonstrates stereocontrolled synthesis of 12a-deoxytetracycline in organic systems, indicating new routes to tetracycline antibiotics.

Key Points

  • Develop a viable, stereocontrolled synthetic route to assemble (±)-12a-deoxytetracycline.
  • Designed a multistep organic synthesis sequence utilizing lactone intermediates and stereoselective cyclization reactions.
  • Controlled relative stereochemistry to construct the characteristic polycyclic framework of deoxytetracycline.
  • Successfully achieved the total stereocontrolled chemical synthesis of racemic 12a-deoxytetracycline.
  • Demonstrated efficient construction of the complex tetracyclic carbon skeleton via targeted cyclization protocols.

Cite This Study

Stork et al. (1996) studied this question.

synapsesocial.com/papers/6aa6a4b050dab972bddd6eedhttps://doi.org/10.1021/ja960434n
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