Dearomatizing cyclization of arylsulfonylalkoxymethyl lithiums: A route to the podophyllotoxin skeleton

Jonathan Clayden*, Martin N. Kenworthy, Madeleine Helliwell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

42 Citations (Scopus)

Abstract

(Matrix presented) The phenylsulfonyl group promotes the dearomatizing cyclization of tethered organolithiums onto aromatic rings. With an ether tether, the cyclizations create a new tetrahydrofuran ring, and both cyclization and subsequent electrophilic quenches proceed with high levels of diastereoselectivity. The sulfonyl group can be removed from the cyclized products oxidatively or reductively. The dearomatizing cyclization of a naphthyl sulfone was used in the synthesis of a close structural analogue of podophyllotoxin.

Original languageEnglish
Pages (from-to)831-834
Number of pages4
JournalOrganic Letters
Volume5
Issue number6
Early online date26 Feb 2003
DOIs
Publication statusPublished - 20 Mar 2003

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