161988-89-2Relevant articles and documents
Substituted amide phenol compound and its preparation method, pharmaceutical composition and use thereof
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Paragraph 0225; 0230-0233, (2019/07/04)
The invention discloses substituted-amide phenolic compounds, their preparation method, a pharmaceutical composition and an application thereof. The compounds have a structure as shown in the general formula I, wherein Z, L and Q are as defined in the spe
Total synthesis of (+)-trans-trikentrin A
Tébéka, Iris R. M.,Longato, Giovanna B.,Craveiro, Marcus V.,De Carvalho, Jo?o E.,Ruiz, Ana L. T. G.,Silva Jr., Luiz F.
, p. 16890 - 16901 (2013/03/14)
Several syntheses have already been reported for cis-trikentrins and herbindoles, which are indole alkaloids unsubstituted at the C2 and C3 positions that bear a trans-1,3-dimethylcyclopentyl unit. Herein, we describe the first asymmetric and stereoselective synthesis of the more challenging trans-trikentrin A as its naturally occurring isomer. Different approaches were investigated and the strategy of choice was a combination of an enzymatic kinetic resolution and a thallium(III)-mediated ring contraction. The antiproliferative activities of the natural product and related intermediates have been tested against human tumor cell lines, leading to the discovery of new compounds with potent antitumor activity. Simple target? Take a look again! The first stereoselective synthesis of a trans-trikentrin is described (see scheme). In contrast, all cis-related natural products have already been synthesized. An enzymatic kinetic resolution and a ring contraction are the key steps. Potent antitumor compounds have been discovered during this study. Copyright
A diastereoselective total synthesis of trans-trikentrin A: A ring contraction approach
Silva Jr., Luiz F.,Craveiro, Marcus V.
supporting information; experimental part, p. 5417 - 5420 (2009/06/06)
(Chemical Equation Presented) A new route to obtain the polyalkylated indole (±)-trans-trikentrin A was developed. The synthesis of this natural alkaloid features a thallium(III)-mediated ring contraction reaction to obtain the trans-1,3-disubstituted five-membered ring in a diastereoselective manner. Thallium(III) is chemoselective in this rearrangement, reacting with the olefin without oxidation of the indole moiety. Other key transformations are the Bartoli's reaction to construct the heterocyclic ring and a Heck coupling to add the carbons atom that will originate the nonaromatic cycle.