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Late‐Stage Bromination Enables the Synthesis of Rubrolides B, I, K, and O
Author(s) -
Karak Milandip,
Acosta Jaime A. M.,
Barbosa Luiz C. A.,
Boukouvalas John
Publication year - 2016
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.201600473
Subject(s) - halogenation , chemistry , regioselectivity , aldol condensation , aldol reaction , suzuki reaction , total synthesis , condensation , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , palladium , physics , thermodynamics
A concise and efficient synthesis of the marine natural products rubrolides B, I, K, and O was accomplished in 3–4 steps from commercially available 3,4‐dichloro‐2(5 H )‐furanone. Key steps include: (i) a site‐selective Suzuki cross‐coupling, (ii) a vinylogous aldol condensation, and (iii) a late‐stage bromination. The latter reaction allowed functionalization of the aromatic rings in a highly regioselective fashion, enabling rapid access to the target rubrolides from common precursors.