Katrina S. Madden
A low temperature, vinylboronate ester-mediated, iterative cross-coupling approach to xanthomonadin polyenyl pigment analogues
Madden, Katrina S.; Knowles, Jonathan P.; Whiting, Andrew
Abstract
Approaches to the polyene natural product xanthomonadin, an octaenyl electron-deficient bacterial photoprotective agent, and its debromo analogue, were developed. These involved the iterative cross-coupling of multiple C2-fragments, using a vinylboronate ester as a formal vinyl dianion equivalent. Vinyl iodide starting materials undergo Heck-Mizoroki cross-coupling at ambient temperatures, allowing further iododeboronation to derive the next vinyl iodide. This works in a highly effective manner to access systems of up to pentaene chain length. However, final assembly of polyenylboronates with such polyenyl iodides through their Suzuki-Miyaura cross-coupling was less successful, even at lower temperatures, reflecting the extreme sensitivity of such octaenylxanthomonadin analogues. Despite this, the mild cross-coupling conditions could be effectively applied to the assembly of a range of useful polyenyl building blocks, as well as a truncated pentaenyl-debromoxanthomonadin analogue.
Citation
Madden, K. S., Knowles, J. P., & Whiting, A. (2019). A low temperature, vinylboronate ester-mediated, iterative cross-coupling approach to xanthomonadin polyenyl pigment analogues. Tetrahedron, 75(45), Article 130657. https://doi.org/10.1016/j.tet.2019.130657
| Journal Article Type | Article |
|---|---|
| Acceptance Date | Sep 26, 2019 |
| Online Publication Date | Oct 3, 2019 |
| Publication Date | Nov 30, 2019 |
| Deposit Date | Oct 14, 2019 |
| Publicly Available Date | Oct 3, 2020 |
| Journal | Tetrahedron |
| Print ISSN | 0040-4020 |
| Publisher | Elsevier |
| Peer Reviewed | Peer Reviewed |
| Volume | 75 |
| Issue | 45 |
| Article Number | 130657 |
| DOI | https://doi.org/10.1016/j.tet.2019.130657 |
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Copyright Statement
© 2019 This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
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