4.8 Article

Synthesis of Microcin SF608 through Nucleophilic Opening of an Oxabicyclo[2.2.1]heptane

Journal

ORGANIC LETTERS
Volume 12, Issue 17, Pages 3950-3953

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol1017189

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Funding

  1. Swiss National Science Foundation [NF5/2-7723408]
  2. ETH
  3. Novartis
  4. Roche Research Foundation

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The total synthesis of Microcin SF608 is reported. Access to the octahydroindole core structure of Microcin SF608 relies on the TMSOTf/NEt3-mediated opening of an oxabicyclic ring system. Additional highlights of the synthetic strategy that is reported include a highly regioselective epoxide reduction and photolytic excision of a 3 alcohol.

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