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
Volume84
Issue18
Pagination12246-12252
Date Published2019 09 20
ISSN1520-6904
Abstract

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.

DOI10.1021/acs.joc.9b02043
Alternate JournalJ Org Chem
PubMed ID31448911