The catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone.
Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.
McFadden
Ryan M
RM
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Stoltz
Brian M
BM
D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology; D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry; D027561:Salvia miltiorrhiza / Q000737:chemistry*; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; C516091:dichroanone; D010165:Palladium