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Updated: Jun 3, 2026
A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
A convergent total synthesis of (±)-γ-rubromycin
Kun-Liang Wu1, Eduardo V Mercado, Thomas R R Pettus
1Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.
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.
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