Synfacts 2019; 15(03): 0221
DOI: 10.1055/s-0037-1611196
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Concise Four-Step Total Synthesis of (±)-Carpanone

Erick M. Carreira
Moritz Hönig
Chapman OL. * Engel MR, Springer JP, Clardy JC. Iowa State University, USA
The Total Synthesis of Carpanone.

J. Am. Chem. Soc. 1971;
93: 6696-6698
Further Information

Publication History

Publication Date:
15 February 2019 (online)



Isolated from the bark of the carpano tree, (±)-carpanone possesses significant structural complexity in the form of five contiguous stereocenters and six rings. Inspired by the proposed biosynthesis (G. C. Brophy et al. Tetrahedron Lett. 1969, 10, 5159), Chapman et al. established that the target can be formed in a single step by oxidation of the simple and achiral precursor D.



Known 6-allylsesamol (C), accessible from sesamol in two steps, was transformed into phenol D by double bond migration under basic conditions. Treatment with PdCl2 effected oxidative phenolic coupling, followed by an intramolecular inverse-electron-demand hetero-Diels–Alder reaction to set all five contiguous stereocenters and furnish the target structure.