Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

Joseph J. Topczewski, John G. Kodet, David F. Wiemer

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandemelectrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.

Original languageEnglish (US)
Pages (from-to)909-919
Number of pages11
JournalJournal of Organic Chemistry
Volume76
Issue number3
DOIs
StatePublished - Feb 4 2011

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