Approaches to Styrenyl Building Blocks for the Synthesis of Polyene Xanthomonadin and its Analogues
Madden, K.S.; Laroche, B.; David, S.; Batsanov, A.S.; Thompson, D.; Knowles, J.P.; Whiting, A.
Dr Andrei Batsanov email@example.com
Professor Andrew Whiting firstname.lastname@example.org
A number of aryl building blocks for the synthesis of two xanthomonadin natural product pigments, as well as a related analogue, were accessed using a divergent hydroboration/bromoboration approach from a key alkynyl intermediate. A new approach towards substitution patterns around the ring was adopted following the isolation of an unexpected regioisomer from the bromination reaction. Potential coupling reactions onto these building blocks were explored, with a successful Sonogashira coupling performed on the key alkynyl intermediate, and with the key debrominated styrenyl boronate ester intermediate functionalised both by preliminary Suzuki–Miyaura coupling and by iododeboronation/Heck–Mizoroki coupling. Coupling reactions with brominated styrenyl intermediates proved much more challenging due to the instability of the intermediates to cross‐coupling, but some studies have shown promise.
Madden, K., Laroche, B., David, S., Batsanov, A., Thompson, D., Knowles, J., & Whiting, A. (2018). Approaches to Styrenyl Building Blocks for the Synthesis of Polyene Xanthomonadin and its Analogues. European Journal of Organic Chemistry, 2018(38), 5312-5322. https://doi.org/10.1002/ejoc.201800540
|Journal Article Type||Article|
|Acceptance Date||Aug 9, 2018|
|Online Publication Date||Oct 7, 2018|
|Publication Date||Oct 17, 2018|
|Deposit Date||Sep 4, 2018|
|Publicly Available Date||Oct 7, 2019|
|Journal||European Journal of Organic Chemistry|
|Peer Reviewed||Peer Reviewed|
Accepted Journal Article
© 2018 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Published Journal Article
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