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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.

Approaches to Styrenyl Building Blocks for the Synthesis of Polyene Xanthomonadin and its Analogues Thumbnail


Authors

K.S. Madden

B. Laroche

S. David

D. Thompson

J.P. Knowles



Abstract

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.

Citation

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
Print ISSN 1434-193X
Electronic ISSN 1099-0690
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2018
Issue 38
Pages 5312-5322
DOI https://doi.org/10.1002/ejoc.201800540
Public URL https://durham-repository.worktribe.com/output/1350175

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Copyright Statement
© 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.






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