A Convergent Total Synthesis of (+)-Ineleganolide

A Convergent Total Synthesis of (+)-Ineleganolide

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 145; no. 14; pp. 7763 - 7767
Main Authors: Gross, Benjamin M., Han, Seo-Jung, Virgil, Scott C., Stoltz, Brian M.
Format: Journal Article
Language:English
Published: United States American Chemical Society 12-04-2023
Subjects:
Communication
Cyclization
Diterpenes
Oxidation-Reduction
Online Access:Get full text
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Summary: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.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c02142