Stereoselective Synthesis of cis- and trans-2,3-Disubstituted Tetrahydrofurans via Oxonium-Prins Cyclization: Access to the Cordigol Ring System

Alan C. Spivey, Luca Laraia, Andrew R. Bayly, Henry S. Rzepa, Andrew J. P. White

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

SnBr4-promoted oxonium-Prins cyclizations to form 2,3-disubstituted tetrahydrofurans (THFs) are reported. In the absence of an internal nucleophile, the carbocation intermediates are trapped by bromide to give 2,3-cis- and 2,3-trans-configured products; two variations with intramolecular trapping are also reported. One of these allows a single-step stereocontrolled synthesis of the core 2,3-cis-THF ring system of cordigol, a fungicidal polyphenol from the stem bark of Cordia goetzei. For this latter transformation, a stepwise oxonium-Prins/cation trapping pathway rather than orthoquinonemethide formation/hetero-Diels-Alder cycloaddition is supported computationally.
Original languageEnglish
JournalORGANIC LETTERS
Volume12
Issue number5
Pages (from-to)900-903
ISSN1523-7060
DOIs
Publication statusPublished - 2010
Externally publishedYes

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