Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C

Jackson A. Gartman, Uttam K. Tambar

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

This manuscript describes our studies of the class of natural products known as the rubellins, culminating in the total synthesis of (+)-rubellin C. These anthraquinone-based natural products contain a variety of stereochemical and architectural motifs, including a 6-5-6-fused ring system, 5 stereogenic centers, and a central quaternary center. Herein, we report our development of a strategy to target the stereochemically dense core and anthraquinone nucleus, including approaches such as a bifunctional allylboron and vinyl triflate reagent, an anthraquinone benzylic metalation strategy, and a late-stage anthraquinone introduction strategy. Our studies culminate in a successful route to highly functionalized anthraquinone-based natural product scaffolds and a stereoselective total synthesis of (+)-rubellin C. These strategies and outcomes will aid in synthetic planning toward anthraquinone-based natural products of high interest.

Original languageEnglish (US)
Pages (from-to)11237-11262
Number of pages26
JournalJournal of Organic Chemistry
Volume86
Issue number16
DOIs
StatePublished - Aug 20 2021

ASJC Scopus subject areas

  • Organic Chemistry

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