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Approaches to Styrenyl Building Blocks for the Synthesis of Polyene Xanthomonadin and its Analogues
Author(s) -
Madden Katrina S.,
Laroche Benjamin,
David Sylvain,
Batsanov Andrei S.,
Thompson Daniel,
Knowles Jonathan P.,
Whiting Andrew
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800540
Subject(s) - chemistry , polyene , sonogashira coupling , combinatorial chemistry , halogenation , suzuki reaction , hydroboration , aryl , structural isomer , ring (chemistry) , organic chemistry , catalysis , palladium , alkyl
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.