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A Convergent Total Synthesis of (+)-Ineleganolide.

ABSTRACT: We report the total synthesis of the furanobutenolide-derived diterpenoid (+)-ineleganolide. The synthetic approach relies on a convergent strategy based on the coupling of two enantioenriched fragments, which are derived from (-)-linalool and (+)-norcarvone, respectively. A high-yielding, one-step Michael addition and aldol cascade furnishes a pentacyclic framework as a single diastereomer, thereby overcoming previous challenges in controlling stereochemistry. The endgame features an O₂-facilitated C-H oxidation and a samarium diiodide-induced semipinacol rearrangement to furnish the highly rigid central seven-membered ring.

SUBMITTER: Gross BM

PROVIDER: S-EPMC10544024 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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A Convergent Total Synthesis of (+)-Ineleganolide.

Gross Benjamin M BM Han Seo-Jung SJ Virgil Scott C SC Stoltz Brian M BM

Journal of the American Chemical Society 20230329 14

We report the total synthesis of the furanobutenolide-derived diterpenoid (+)-ineleganolide. The synthetic approach relies on a convergent strategy based on the coupling of two enantioenriched fragments, which are derived from (-)-linalool and (+)-norcarvone, respectively. A high-yielding, one-step Michael addition and aldol cascade furnishes a pentacyclic framework as a single diastereomer, thereby overcoming previous challenges in controlling stereochemistry. The endgame features an O<sub>2</s ...[more]

PMID: 36989438

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Correction: Enantioselective, convergent synthesis of the ineleganolide core by a tandem annulation cascade.

Project description:[This corrects the article DOI: 10.1039/C6SC03347D.].

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