Access to Highly Strained Tricyclic Ketals Derived from Coumarins

Sravan K. Jonnalagadda, Bader I. Huwaimel, Shirisha Jonnalagadda, Jered C. Garrison, Paul C. Trippier

Research output: Contribution to journalArticlepeer-review

Abstract

Synthesis of highly strained fused substituted dihydrobenzopyran cyclopropyl lactones derived from coumarin carboxylates are reported. The substrate scope tolerates a variety of 6- and 8-substituents on the coumarin ring. Substitution at the 5- or 7-position is resistant to tricyclic lactone formation except with 7-methyl substitution. Benzamide-containing coumarins afford the tricyclic ketal. A plausible mechanism is proposed for the formation of the fused lactone: intramolecular rearrangement of trans cyclopropyl methyl ketones with phenolic acetate via the formation of a hemiacetal.

Original languageEnglish (US)
Pages (from-to)4476-4482
Number of pages7
JournalJournal of Organic Chemistry
Volume87
Issue number6
DOIs
StatePublished - Mar 18 2022

ASJC Scopus subject areas

  • Organic Chemistry

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