Title | Synthetic Studies toward Bazzanin K: Regioselective and Chemoselective Three-Component Suzuki Coupling. |
Publication Type | Journal Article |
Year of Publication | 2019 |
Authors | Ju X, Allen M, Zhao P, Salvo P, Dyer FB, Beaudry CM |
Journal | J Org Chem |
Volume | 84 |
Issue | 18 |
Pagination | 12246-12252 |
Date Published | 2019 09 20 |
ISSN | 1520-6904 |
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. |
DOI | 10.1021/acs.joc.9b02043 |
Alternate Journal | J Org Chem |
PubMed ID | 31448911 |