4.8 Article

Total Synthesis of des-Thiomethyllooekeyolide A

Journal

ORGANIC LETTERS
Volume 24, Issue 40, Pages 7260-7264

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02412

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Funding

  1. Guangdong Department of Education [2021ZDJS097]
  2. Guangdong Basic and Applied Basic Research Foundation [2021A1515010188]
  3. National Institutes of Health [R01CA172310]

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The first asymmetric total synthesis and validation of the structural assignment of des-thiomethyllooekeyolide A (3) is described, which involves a Shiina macrolactonization and a late-stage pyran-hemiketal formation. The eight stereogenic centers of the C16-polyketide chain were installed by sequential aldol and crotylation reactions.
The first asymmetric total synthesis and validation of the structural assignment of des-thiomethyllooekeyolide A (3) is described, which features a Shiina macrolactonization and a late-stage pyran-hemiketal formation. The eight stereogenic centers of the C16-polyketide chain were installed by sequential aldol and crotylation reactions.

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