Subscribe to RSS
Synthesis of (–)-Incarviatone A
Enantioselective Total Synthesis of (–)-Incarviatone A.
J. Am. Chem. Soc. 2015;
17 November 2015 (online)
Key words(–)-incarviatone A - C–H bond functionalization - biomimetic cascade - chiral auxiliary - aldol condensation
The natural product hybrid (–)-incarviatone A displays considerable potential for the treatment of depression and neurological disorders. It also features a complex polycyclic core structure with eight contiguous stereogenic centers. In this work, the authors report the first total synthesis relying on a striking biomimetic cascade reaction.
The synthesis commenced with ortho-C–H alkylation of A. Thereafter, trans-indane acid F was obtained by a chiral auxiliary mediated C–H insertion with diazo compound D. Phenolic aldol condensation between H and I and subsequent dearomatization set the stage for a biomimetic cascade that culminated in the total synthesis of (–)-incarviatone A.