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.

doi:10.1002/ejoc.201800540

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.

Authors

K.S. Madden

B. Laroche

S. David

Dr Andrei Batsanov a.s.batsanov@durham.ac.uk
Academic Visitor

D. Thompson

J.P. Knowles

Professor Andrew Whiting andy.whiting@durham.ac.uk
Emeritus Professor

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

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© 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.