476-56-2Relevant articles and documents
Regioselective Synthesis of Islandicin and Digitopurpone
Wiseman, John R.,Pendery, John J.,Otto, Charlotte A.,Chiong, Kaolin G.
, p. 516 - 519 (1980)
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Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C
Gartman, Jackson A.,Tambar, Uttam K.
, p. 11237 - 11262 (2021/08/16)
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.
A VERSATILE SYNTHESIS OF HYDROXY-9,10-ANTHRAQUINONE-2-CARBOXYLIC ACIDS
Smith, Colin W.,Ambler, Samantha J.,Steggles, David J.
, p. 7447 - 7450 (2007/10/02)
Islandicin, a mould metabolite, can be synthesised in a few, robust, high yielding steps.This procedure can be further elaborated to give a variety of hydroxy-9,10-anthraquinone-2-carboxylic acids.
A New Synthesis of Anthraquinones Using Dihydro-oxazoles and Grignard Reagents Derived from Mg(Anthracene)(THF)3
Nicoletti, Teresa M.,Raston, Colin L.,Sargent, Melvyn V.
, p. 133 - 138 (2007/10/02)
A general synthesis of anthraquinones which depends on the displacement of the methoxy group from an o-methoxyaryldihydro-oxazole by a methoxy substituted benzylmagnesium chloride, generated by using a magnesium-anthracene complex, has been developed.The masked benzylbenzoic acids which result from these reactions are deprotected and then ring-closed to anthrones which on oxidation yield anthraquinones.In this way, the followeing naturally occurring anthraquinones (or derivatives thereof have been synthesized): chrysophanol (9), islandicin (19), digitopurpone (21), tri-O-methylemodin (26), and di-O-methylsoranjidiol (29).
