TitleSynthetic Studies toward Bazzanin K: Regioselective and Chemoselective Three-Component Suzuki Coupling.
Publication TypeJournal Article
Year of Publication2019
AuthorsJu X, Allen M, Zhao P, Salvo P, Dyer FB, Beaudry CM
JournalJ Org Chem
Date Published2019 09 20

The terphenyl substructure of the chiral cyclophane natural product bazzanin K was constructed. The key step involved sequential Suzuki couplings of a nonsymmetric dibromobenzene, which can be performed as a two-step process or as a one-pot three-component coupling. The key step represented a regioselective coupling of a dibromobenzene, as well as a chemoselective coupling of phenyl bromides in the presence of phenyl chlorides. Terphenyl intermediates displayed atropdiastereoisomerism, and they were converted to a single phenanthrene target by way of ring-closing metathesis.

Alternate JournalJ Org Chem
PubMed ID31448911