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Synfacts 2015; 11(12): 1231
DOI: 10.1055/s-0035-1560838
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Incarviatone A

Contributor(s):
Erick M. Carreira
,
Stefan Fischer
Hong B, Li C, Wang Z, Chen J, Li H, * Lei X. * Peking University, Beijing, Tianjin University, and National Institute of Biological Sciences, Beijing, P. R. of China
Enantioselective Total Synthesis of (–)-Incarviatone A.

J. Am. Chem. Soc. 2015;
137: 11946-11949
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Further Information

Publication History

Publication Date:
17 November 2015 (online)

 
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Key words

(–)-incarviatone A - C–H bond functionalization - biomimetic cascade - chiral auxiliary - aldol condensation

Significance

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.


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Comment

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.


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