A synthesis-enabled relative stereochemical assignment of the C1-C28 region of hemicalide.

Through synthesising both candidate diastereomers of a model C1-C28 fragment of the potent cytotoxic marine polyketide hemicalide, an assignment of the relative configuration between the C1-C15 and C16-C26 regions has been achieved. By detailed NMR comparisons with the natural product, the relative stereochemistry between these two 1,6-related stereoclusters is elucidated as 13,18-syn rather than the previously proposed 13,18-anti relationship. A flexible and modular strategy using an advanced C1-C28 ketone fragment 22 is outlined to elucidate the remaining stereochemical features and achieve a total synthesis.

• Publication year

  2018

• Venue

  Chemical Communications

• Publication date

  2018-03-27

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1039/c8cc00933cPMID 29536067
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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