62790-79-8Relevant articles and documents
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.
Asymmetric synthesis of novel spirocycles via a chiral phosphoric acid catalyzed desymmetrization
Kelley, Amber M.,Minerali, Eni,Wilent, Jennifer E.,Chambers, Nicholas J.,Stingley, Kyla J.,Wilson, G. Tyler,Petersen, Kimberly S.
supporting information, p. 1262 - 1264 (2019/04/10)
A straightforward method for the asymmetric preparation of novel lactone and lactam spirocycles is described. An initial desymmetrization via a chiral Br?nsted acid yields enantioenriched lactones which readily undergo a second cyclization to give the des
7-MEMBERED FUSED HETEROCYCLES AND METHODS OF THEIR SYNTHESIS
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Paragraph 0101; 0102; 0103, (2015/03/16)
Disclosed are a new method for synthesizing 7-membered fused heterocycles and compounds synthesized by the new method. The method involves a dual activation strategy using an N-heterocyclic carbene catalyst as a first Lewis base and another second Lewis b