Total synthesis of euplectin, a natural product with a chromone fused indenone.
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.
Mal
Dipakranjan
D
Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India. dmal@chem.iitkgp.ernet.in
De
Saroj Ranjan
SR
D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D002867:Chromones / Q000737:chemistry*; D007192:Indenes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001685:Biological Factors; D002867:Chromones; D007192:Indenes; C545155:euplectin