4.7 Review

Stereoselective Construction of (E,Z)-1,3-Dienes and Its Application in Natural Product Synthesis

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 24, Pages 5532-5575

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000730

Keywords

alkenes; 1,3-dienes; E,Z-configuration; natural products; synthetic methods; total synthesis

Funding

  1. Agence Nationale de la Recherche (ANR) [ANR-17-CE07-0051-01]
  2. German Research Foundation (DFG) [BE 4799/2-1, BE 4799/3-1]
  3. Agence Nationale de la Recherche (ANR) [ANR-17-CE07-0051] Funding Source: Agence Nationale de la Recherche (ANR)

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The E,Z-configured 1,3-diene unit is a common motif in numerous bioactive natural products. Although several powerful methods are available to produce these motifs with high levels of selectivity, their construction within a complex, polyfunctionalised structure, such as a natural product, requires well-defined strategies to avoid undesirable reactions and low-to-moderate selectivities. The aim of this review is to provide a full account of the stereoselective strategies for building E,Z-configured 1,3-dienes, as well as to highlight selected total syntheses that employ them.between alpha-lithiated epoxides and Grignard reagents

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