The first stereoselective synthesis of the natural product, rotenone

Autor:	Stephen C. Pelly, Kathy Hadje Georgiou, Charles B. de Koning
Rok vydání:	2017
Předmět:	Natural product 010405 organic chemistry Stereochemistry Organic Chemistry Rotenone Resorcinol 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound chemistry Drug Discovery Munduserone Organic chemistry Stereoselectivity
Zdroj:	Tetrahedron. 73:853-858
ISSN:	0040-4020
DOI:	10.1016/j.tet.2016.12.062
Popis:	The total syntheses of rotenone and munduserone are reported in this paper. The synthesis of rotenone involves two key transformations, the first of which is a Pd π-allyl mediated cyclisation for the construction of the dihydrobenzofuran skeleton. The second is a 6-endo-hydroarylation which yields the chromene as a precursor to rotenone. The synthesis of rotenone was achieved in 17 steps from resorcinol and constitutes the first stereoselective synthesis of this complex natural product.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0ac40a4c52fb63d237eaf1aa118b71e0 https://doi.org/10.1016/j.tet.2016.12.062 Zobrazit plný text záznamu Full Text from ScienceDirect