title: A convergent total synthesis of (±)-γ-rubromycin.
abstract: An expeditious convergent total synthesis affords (±)-γ-rubromycin (1) in 4.4% overall yield. The longest linear sequence is 12 steps from commercial starting materials. The effort highlights a remarkable late-stage oxidative [3 + 2] cycloaddition for construction of the spiroketal, a regioselective carbonyl methylenation, a boron tribromide promoted deprotection, ortho- to para- naphthoquinone spiroketal rearrangement, and a tautomerization sequence.
authors: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.
authors: Kun-Liang
authors: KL
authors: Wu
authors: Eduardo V
authors: EV
authors: Mercado
authors: Thomas R R
authors: TR
authors: Pettus
mesh_terms: D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis*
chemical_list: D011809:Quinones; C064949:gamma-rubromycin