94975-03-8Relevant academic research and scientific papers
BENZAMIDE DIRECTED ORTHO METALATION. A ROUTE TO THE A/B RING SYNTHON OF DAUNOMYCINONE.
Sibi, Mukund P.,Altintas, N.,Snieckus, V.
, p. 4593 - 4596 (1984)
The A/B ring synthon 13, previously converted into daunomycinone (6) by Keay and Rodrigo, has been prepared in seven steps and 38percent overall yield using benzamide directed ortho metalation strategy.Significant steps are:the incorporation of a four-car
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 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
A regioselective synthesis of dimethyl phthalide-3-phosphonates
Watanabe,Ijichi,Furukawa
, p. 94 - 98 (2007/10/02)
Dimethyl phthalide-3-phosphonates having various substituents on the benzene ring were regioselectively synthesized by the reaction of N,N-diethyl-2-formylbenzamides with tert-butyldimethylsilyl dimethyl phosphite followed by treatment with methanesulfonic acid. N,N-Diethyl-2-formylbenzamides were regioselectively prepared by ortho lithiation-formylation of the corresponding benzamides.
