Towards a total synthesis of the new anticancer agent mensacarcin: synthesis of the carbocyclic core

Chemistry : a European Journal
Lutz F TietzeAxel Zeeck

Abstract

A synthesis of the carbocyclic core associated with the new anticancer agent mensacarcin (1) is reported. The strategy involves the synthesis of several novel highly substituted aromatic compounds, such as 12 and 23. The lithium derivative of 12 readily engages in a nucleophilic addition to benzaldehyde 4 to provide the diphenylcarbinol rac-15. The analogous benzyl ether rac-16 undergoes an intramolecular Heck reaction to provide the required tetrahydroanthracene rac-17, which can be transformed into the key tricyclic methyl ether rac-20. In a second approach, the lithium derivative of 21 is added to the hexasubstituted benzaldehyde 23 to give the diphenylcarbinol rac-35. Subsequent methylation to rac-36 followed by an intramolecular Heck reaction provides tricycle rac-37. Similarly, the oxidised compound 40 provides an electronically more suitable intramolecular Heck partner to afford compound 41. Further transformations of these substrates leads to rac-43, which incorporates the core structure of mensacarcin (1).

Citations

Sep 11, 2013·ACS Chemical Biology·Bastian BlauenburgMikko Metsä-Ketelä
Oct 28, 2017·The Journal of Biological Chemistry·Birte PlitzkoSandra Loesgen
Feb 21, 2014·Chembiochem : a European Journal of Chemical Biology·Sarah MaierAndreas Bechthold
Jun 21, 2008·Chemical Communications : Chem Comm·Alois Fürstner, Jens Ackerstaff
Dec 14, 2011·Chembiochem : a European Journal of Chemical Biology·Xiaohui YanAndreas Bechthold
Apr 25, 2015·Chembiochem : a European Journal of Chemical Biology·Sarah MaierAndreas Bechthold
Jan 25, 2013·Chemistry : a European Journal·Yinjun ZouJianrong Steve Zhou
Jun 9, 2005·Chemical Reviews·Jairton DupontJohn Spencer
May 15, 2013·Organic Letters·Deniz Arican, Reinhard Brückner

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