41722-49-0Relevant articles and documents
Studies towards the Total Synthesis of Kadcotrione B
Gangababu, Marri,Manimala, Patel,Rammohan, Aluru,Reddy, Julakanti Satyanarayana,Yadav, Jillu Singh
, p. 735 - 743 (2020)
A convergent and efficient approach towards the total synthesis of Kadcotrione B is described. For this purpose, the syntheses of two fragments, 6/6/5-fused tricyclic ring and C-9 side chain, were accomplished. The salient features of these syntheses are
Enantioselective synthesis and complement inhibitory assay of A/B-ring partial analogues of oleanolic acid
Assefa, Haregewein,Nimrod, Alison,Walker, Larry,Sindelar, Robert
, p. 1619 - 1623 (2001)
A series of oleanolic acid A/B-ring partial analogues was synthesized and tested for their complement inhibitory activity as well as cytotoxic properties. All target compounds and one intermediate exhibited moderate complement inhibitory potency. These co
SYNTHESIS OF BRUCEANTIN SKELETON
Murae, Tatsushi,Sasaki, Makoto,Konosu, Toshiyuki,Matsuo, Hisaaki,Takahashi, Takeyoshi
, p. 3411 - 3414 (1986)
A stereoselective synthesis of a compound (3), which satisfies all requirements for bruceantin skeleton and has preferable functional groups at suitable positions for the total synthesis of bruceantin, is described.
Total Synthesis of Kadcoccinic Acid A Trimethyl Ester
Trost, Barry M.,Zhang, Guoting,Gholami, Hadi,Zell, Daniel
, p. 12286 - 12293 (2021/08/20)
The first total synthesis of the trimethyl ester of kadcoccinic acid A is described. The central structural element of our synthesis is a cyclopentenone motif that allows the assembly of the natural product skeleton. A gold(I)-catalyzed cyclization of an enynyl acetate led to efficient construction of the cyclopentenone scaffold. In this step, optimization studies revealed that the stereochemistry of the enynyl acetate dictates regioisomeric cyclopentenone formation. The synthesis further highlights an efficient copper-mediated conjugate addition, merged with a gold(I)-catalyzed Conia-ene reaction to connect the two fragments, thereby forging the D-ring of the natural product. The synthetic strategy reported herein can provide a general platform to access the skeleton of other members of this family of natural products.
Total Synthesis of Paspaline A and Emindole PB Enabled by Computational Augmentation of a Transform-Guided Retrosynthetic Strategy
Kim, Daria E.,Zweig, Joshua E.,Newhouse, Timothy R.
, p. 1479 - 1483 (2019/01/26)
We report the total syntheses of two indole diterpenoid natural products, paspaline A and emindole PB. Paspaline A is synthesized in a 9-step sequence from commercially available materials. The first total synthesis of emindole PB is accomplished in 13 steps and confirms a previously ambiguous structural assignment. Density functional theory calculations are utilized to interrogate the key carbocationic rearrangement in a predictive capacity to aid in the selection of the most favorable precursor substrate. This work highlights how retrosynthetic design can be augmented with quantum chemical calculations to reveal energetically feasible synthetic disconnections, minimizing time-consuming and expensive empirical evaluation.
TETRAHYDRONAPHTHALENE DERIVATIVES USEFUL AS NRF2 ACTIVATORS
-
, (2019/06/11)
Provided are compounds of Formula I, or pharmaceutically acceptable salts thereof, and methods for their use as Nrf2 activators and for their production.
Pinacol Coupling Strategy for the Construction of the Bicyclo[6.4.1]tridecane Framework of Schiglautone A
Werner, Bettina,Kalesse, Markus
, p. 1524 - 1526 (2017/04/13)
The synthesis of the tricyclic carbon framework of schiglautone A (1) is reported herein. The generation of the bicyclo[6.4.1]tridecane 19 was accomplished via a SmI2-mediated pinacol coupling of dialdehyde 18. The side chain in 18 was introduc
Gaining Synthetic Appreciation for the Gedunin ABC Ring System
Pinkerton, David M.,Vanden Berg, Timothy J.,Bernhardt, Paul V.,Williams, Craig M.
supporting information, p. 2282 - 2285 (2017/02/23)
Gedunin, first isolated in 1960, displays a remarkable range of biological activity, but has yet to receive dedicated synthetic attention from a ground up construction perspective. Presented herein is a successfully executed approach to the fully function
A Highly Active Polymer-Supported Catalyst for Asymmetric Robinson Annulations in Continuous Flow
Canellas, Santiago,Ayats, Carles,Henseler, Andrea H.,Pericàs, Miquel A.
, p. 1383 - 1391 (2017/08/09)
The preparation through Robinson annulation of enantiopure building blocks with both academic and industrial relevance, such as the Wieland-Miescher and Hajos-Parrish ketones, has suffered from important drawbacks, such as the need for high catalyst loading or extremely long reaction times. Here we report a heterogenized organocatalyst based on Luo's diamine for fast and broad-scope enantioselective Robinson annulation reactions. The polystyrene-supported diamine 19a enables the high-yield, highly enantioselective preparation of a wide range of chiral bicyclic enones under mild conditions, with reaction times as short as 60 min (batch) or residence times of 10 min (flow). In contrast with its homogeneous counterpart 19b, the catalytic resin 19a experiences a notable increase in catalytic activity with temperature in 2-MeTHF (a 10-fold decrease in reaction times without erosion in enantioselectivity is observed from room temperature to 55 °C). The scope of the transformation in batch mode has been illustrated with 14 examples, including examples only reported in poorly enantioenriched (22n) or in racemic form (22k). Enantiopure 22k has been used as the starting material for a straightforward formal synthesis of the antibiotic and antifeedant sesquiterpene (-)-isovelleral (24). The heterogenized catalyst 19a admits extended recycling (10 cycles) and has been used to develop the first asymmetric Robinson annulations in continuous flow. The potential of the flow process is illustrated by the large-scale preparation of the Wieland-Miescher ketone (65 mmol in 24 h of operation, TON of 117) and by a sequential flow experiment leading to a library of eight enantioenriched diketone compounds.
Total synthesis of dysidavarone A
Yu, Chunhui,Zhang, Xiaoguang,Zhang, Jinghua,Shen, Zhengwu
, p. 4337 - 4345 (2016/07/06)
Dysidavarone A is a sesquiterpene isolated from the South China Sea sponge Dysidea avara and was reported that it showed significant anticancer activities. Because the compound has unique ‘dysidavarane’ carbon skeleton and potent biological activity, a se