72003-93-1Relevant academic research and scientific papers
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.
Annulations with Butenolides and Phthalides: New Entries to Isocoumarins, 3,4-Dihydroisocoumarins, and Benzofurans
Wang, Shuai,Kraus, George A.
, p. 2821 - 2827 (2020/07/30)
The reactions of the anions of butenolides and substituted phthalides with sorbate esters and mono-epoxy sorbate esters furnish isocoumarins, 3,4-dihydroisocoumarins, and benzofurans. The yields range from 41% to 71%.
Total synthesis of sparstolonin B via a palladium-catalyzed aldehyde α-arylation
Kim, Dalton,Nash, Aaron,De Brabander, Jef,Tambar, Uttam K.
supporting information, p. 3787 - 3790 (2018/05/24)
A concise and convergent total synthesis of sparstolonin B was developed. A palladium-catalyzed aldehyde α-arylation was utilized to construct the carbon skeleton of the natural product. A subsequent simple one-pot procedure effected global deprotection and closure of the final two rings via an unusual autoredox mechanism for the conversion of a bis-hydroquinone intermediate to the natural product. The 6 step synthetic sequence was realized in 18% overall yield.
Chemoselective Ruthenium-Catalyzed C-O Bond Activation: Orthogonality of Nickel- and Palladium-Catalyzed Reactions for the Synthesis of Polyaryl Fluorenones
Da Frota, Livia C. R. M.,Schneider, Cédric,De Amorim, Mauro B.,Da Silva, Alcides J. M.,Snieckus, Victor
supporting information, p. 2587 - 2593 (2017/11/28)
Ruthenium-catalyzed C-O bond activation/arylation of methoxy and O -carbamoyl-substituted fluorenones is reported. Established are new reactions of compound 1 (X = H) to aryl (2) and 1,8-diaryl (3) fluorenones. Orthogonal ruthenium-, palladium- and nickel
Beyond directed ortho metalation: Ru-catalyzed CAr-O activation/cross-coupling reaction by amide chelation
Zhao, Yigang,Snieckus, Victor
supporting information, p. 11224 - 11227 (2014/09/29)
Disclosed is a new, catalytic, and general methodology for the chemical synthesis of biaryl, heterobiaryl, and polyaryl molecules by the cross-coupling of o-methoxybenzamides with aryl boroneopentylates. The reaction is based on the activation of the unreactive C-OMe bond by the proximate amide directing group using catalytic RuH2(CO)(PPh3)3 conditions. A one-step, base-free coupling process is thereby established that has the potential to supersede the useful two-step directed ortho metalation/cross- coupling reaction involving cryogenic temperature and strong base conditions. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, minimum waste, and convenient scale-up make these reactions suitable for industrial applications.
Total synthesis of crisamicin A
Li, Zhengtao,Gao, Yingxiang,Tang, Yefeng,Dai, Mingji,Wang, Guoxin,Wang, Zhigang,Yang, Zhen
supporting information; experimental part, p. 3017 - 3020 (2009/04/18)
(Chemical Equation Presented) Stereoselective total synthesis of natural product crisamicin A (1) was accomplished for the first time via the Pd/TMTU-catalyzed alkoxycarbonylative annulation to generate a unique cis-pyran-fused lactone, an intermolecular
Heterocyclic anthracycline analogs
-
, (2008/06/13)
Novel pyrano heterocyclic anthracycline derivatives are described, which are useful in the treatment of cancer and tumors, such as breast cancer, leukemia, lung cancer, colon cancer, ovarian cancer, renal cancer, and melanoma. As well, these compounds may be used ex vivo for the treatment of cancerous bone marrow before retransplanting said marrow in a patient. Pharmaceutical compositions and methods of preparing the compounds are also described.
