title: Rapid Access to Orthogonally Functionalized Naphthalenes: Application to the Total Synthesis of the Anticancer Agent Chartarin.
abstract: We report the synthesis of orthogonally functionalized naphthalenes from simple, commercially available indanones in four steps. The developed method proceeds through a two-step process that features a thermally induced fragmentation of a cyclopropane indanone with simultaneous 1,2-chloride shift. Migration of the chloride substituent occurs in a regioselective manner to preferentially afford the para-chloronaphthol substitution pattern. The obtained naphthols are versatile building blocks that can be selectively modified and used for the efficient construction of biologically active molecules. This has enabled the total synthesis of the potent anticancer natural product chartarin through a highly convergent retrosynthetic bond disconnection.
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377, Munich, Germany.
authors.forename: Teresa A
authors.initials: TA
authors.lastname: Unzner
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377, Munich, Germany.
authors.forename: Adriana S
authors.initials: AS
authors.lastname: Grossmann
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377, Munich, Germany. thomas.magauer@lmu.de.
authors.forename: Thomas
authors.initials: T
authors.lastname: Magauer
keywords: arenes; naphthalenes; natural products; ring expansion; total synthesis