A Paternò-Büchi approach to the synthesis of merrilactone A

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Abstract

(Chemical Equation Presented) A six-step approach to the tetracyclic core of merrilactone A is described that uses an intramolecular Paternò- Büchi photoaddition to install the key oxetane ring. Irradiation of bicyclic enone 16, constructed through cyclopentenone alkylation followed by a domino oxy-/carbopalladation reaction, produces the tetracyclic oxetane 17 in excellent yield, having the core carbon skeleton of the target compound merrilactone A. © 2005 American Chemical Society.

Bibliographical metadata

Original languageEnglish
Pages (from-to)3969-3971
Number of pages2
JournalOrganic Letters
Volume7
Issue number18
DOIs
StatePublished - 1 Sep 2005