Total Synthesis of (+)-Rubellin C

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2020 Aug 19

PMID 32806220

Citations 2

Authors

Jackson A Gartman

Uttam K Tambar

Affiliations

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Abstract

The rubellins are a family of stereochemically complex anthraquinoid heterodimers containing an unprecedented chemical scaffold. Although the rubellins have been known for over three decades, no total synthesis has been achieved since their discovery. Their topology is characterized by a 6-5-6 fused ring system, five neighboring stereocenters including a quaternary center all in a convoluted core, and an anthraquinone nucleus. The rubellin architecture has been shown to inhibit and reverse the aggregation of tau protein, a therapeutically relevant target for Alzheimer's disease. Herein, we describe the first stereoselective synthesis of a member of the family, (+)-rubellin C, in 16 steps. Strategic disconnections allow expedient construction of stereochemical and topological intricacy in a short sequence of borylative and transition metal-catalyzed steps.

Citing Articles

Recent total syntheses of anthraquinone-based natural products.

Gartman J, Tambar U Tetrahedron. 2022; 105.

PMID: 35095120 PMC: 8794305. DOI: 10.1016/j.tet.2021.132501.

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

Gartman J, Tambar U J Org Chem. 2021; 86(16):11237-11262.

PMID: 34288689 PMC: 8650140. DOI: 10.1021/acs.joc.1c00920.

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