36831-93-3Relevant academic research and scientific papers
Synthesis of (±)-Idarubicinone via Global Functionalization of Tetracene
Dennis, David G.,Okumura, Mikiko,Sarlah, David
supporting information, p. 10193 - 10198 (2019/07/05)
Anthracyclines are archetypal representatives of the tetracyclic type II polyketide natural products that are widely used in cancer chemotherapy. Although the synthesis of this class of compounds has been a subject of several investigations, all known approaches are based on annulations, relying on the union of properly prefunctionalized building blocks. Herein, we describe a conceptually different approach using a polynuclear arene as a starting template, ideally requiring only functional decorations to reach the desired target molecule. Specifically, tetracene was converted to (±)-idarubicinone, the aglycone of the FDA approved anthracycline idarubicin, through the judicious orchestration of Co- and Ru-catalyzed arene oxidation and arenophile-mediated dearomative hydroboration. Such a global functionalization strategy, the combination of site-selective arene and dearomative functionalization, provided the key anthracycline framework in five operations and enabled rapid and controlled access to (±)-idarubicinone.
Formation of arenes via diallylarenes: Strategic utilization of Suzuki-Miyaura cross-coupling, Claisen rearrangement and ring-closing metathesis
Kotha, Sambasivarao,Shah, Vrajesh R.,Mandal, Kalyaneswar
, p. 1159 - 1172 (2008/04/03)
Two new synthetic strategies for benzoannulation are reported. The first strategy is based on the Suzuki-Miyaura cross-coupling reaction. To this end, various ortho-diallylbenzene derivatives were prepared from the corrresponding diiodo derivatives by an allylation strategy using an allylboronate as coupling partner. These diallyl derivatives were subjected to a ring-closing metathesis (RCM) and one-pot dichlorodicyanoquinone (DDQ) oxidation sequence to deliver 2-substituted naphthalenes. In the second strategy, a double Claisen rearrangement and RCM protocol have been used as key steps to give highly functionalized benzoannulated quinone derivatives.
A new protocol for benzoannulation by double Claisen rearrangement and ring-closing metathesis reactions as key steps
Kotha, Sambasivarao,Mandal, Kalyaneswar
, p. 2585 - 2588 (2007/10/03)
A new methodology for benzoannulation has been developed by using double Claisen rearrangement followed by a one-pot ring-closing metathesis and DDQ oxidation sequence.
Tetracene Derivatives as Potential Red Emitters for Organic LEDs
Odom, Susan A.,Parkin, Sean R.,Anthony, John E.
, p. 4245 - 4248 (2007/10/03)
(Equation presented) As part of our program investigating the use of ethynylated acenes in organic electronics, we have prepared a series of functionalized tetracene derivatives in search of a material with red emission suitable for use in display technologies. A number of such compounds with functionalization on the alkyne and/or the acene ring were easily prepared in one or two steps from commercially available materials. Solution fluorescence quantum efficiencies were generally good for these derivatives, which possessed emission maxima spanning the range 540-637 nm. Simple light-emitting diodes fabricated from these compounds showed that one of the derivatives did exhibit red electroluminescence.
Experiments Directed Towards the Synthesis of Anthracyclinones. XX. Titanium(IV)- and Tin(IV)-Mediated Cyclizations of ortho-Allyl-Substituted Homochiral Dioxans
Cambie, Richard C.,Higgs, Kerianne C.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 1295 - 1320 (2007/10/02)
Titanium(IV) chloride mediated cyclization of the ortho-methoxylated 1,3-dioxan (5) gives a high yield of a mixture (10:1) of the (7R)-tetracycles (18) and (19) which are epimeric at C 9.The exclusive formation of the (7R) stereochemistry results from Ss
