Toward the synthesis of phomoidride D

Graham K. Murphy, Tatsuya Shirahata, Naoto Hama, Aaron Bedermann, Ping Dong, Travis C. McMahon, Barry M. Twenter, David A. Spiegel, Ivar M. McDonald, Nobuaki Taniguchi, Munenori Inoue, John L. Wood

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.

Original languageEnglish
Pages (from-to)477-489
Number of pages13
JournalJournal of Organic Chemistry
Volume78
Issue number2
DOIs
Publication statusPublished - 2013 Jan 18

ASJC Scopus subject areas

  • Organic Chemistry

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