Total Synthesis of Euplectin, a Natural Product with a Chromone Fused Indenone
Organic Letters2009Vol. 11(19), pp. 4398–4401
Citations Over TimeTop 10% of 2009 papers
Abstract
The first total synthesis of euplectin, a rare metabolite with a chromone annulated indenone motif, has been accomplished in 17 steps. This has been possible through interplay among three key reactions: a Hauser sulfoxide annulation, a new chromone formation and a late-stage retro-Diels-Alder reaction. The entire regiochemical integrity of the successful route is established by an iodine-catalyzed aromatization of a cyclohexane-1,3-dione and the Hauser annulation.
Related Papers
- → Total Synthesis, Structure Revision, and Absolute Configuration of (+)-Yatakemycin(2004)99 cited
- → Total Synthesis of the Chlorinated Marine Natural Product Dysamide B(2006)57 cited
- → Rapid Generation of Molecular Complexity by Chemical Synthesis: Highly Efficient Total Synthesis of Hexacyclic Alkaloid (−)‐Chaetominine and Its Biosynthetic Implications(2018)11 cited
- → Total Synthesis of a Marine Macrolide Natural Product, Iriomoteolide-2a: The Fundamental Role of Total Synthesis in Natural Product Chemistry(2019)2 cited
- → ChemInform Abstract: Merging Chemical Synthesis and Biosynthesis: A New Chapter in the Total Synthesis of Natural Products and Natural Product Libraries(2012)