Synthesis of Hepta-1,3,6-trien-5-ols for potential 8π electrocyclizations

• Author(s) / Creator(s)

  • Kirk, Bryce J.

• Hepta-1,3,6-trien-5-ols have the potential to act as electrocyclization precursors in anionic 7 carbon/8π conrotatory transformations. A concise synthesis of these trienol substrates is discussed. The sequence of Vilsmeier Haack type reaction, 1,2-vinyl addition, and a Suzuki-Miyaura cross-coupling allows for multiple points of elaboration and alkenyl stereocontrol. Finally, the alcohol can be converted to groups such as silyl ethers or carbamates to probe the impact on carbolithiation.

• Date created

  2021-04-16

• Subjects / Keywords

  • electrocyclization
  • synthesis
  • method development
  • 1,2-vinyl addition
  • Suzuki coupling

• Type of Item

  Conference/Workshop Poster

• DOI

  https://doi.org/10.7939/r3-agjv-df25

• License

  Attribution-NonCommercial 4.0 International