Practical Synthesis of p‐ and o‐Amino‐ and Methoxyphenolic Anthraquinones

Abstract

New versatile and selective methods for the syntheses of substituted amino- and methoxyphenolic anthraquinones (I-IV) based on fusion of cyanophthalides (V) and semiquinone aminals (VI, VII) under basic conditions are described.

Isolation and identification of Anthraquinones from the roots of Morinda Morindoides (Rubiaceae)

“…The structure of the compound 1 was identified as 4-hydroxy-1-methoxy-2-methyl Anthraquinone (named morindin). It was identical to a synthetic Anthraquinone obtained by the reaction of phtalide anions with Quinone monoacetals [11] and the reaction of 3-cyano-1(3H)isobenzofuranone with N-methyl-p-methoxy semi Quinone animal [12] . From a chemotaxonomic viewpoint, similar 1, 2, 4trisubstituted B-ring anthraquinones, such as 1 were obtained in Prismatomeris Connata [21,22] , Digitlis lanata [23] and Tectona grandis [24] belonging respectively to Rubiaceae, Scrophulariaceae and Verbenaca family.…”

“…The ethyl acetate extract showed significant plasmodial and antidiarrheal activity [6,9,10] . In this present paper, we report the isolation and identification of the Anthraquinone, 4-hydroxy-1-methoxy-2methylanthraquinone (1) from a natural source which was identical to a known synthetic product [11,12] .…”

The Evolution and Impact of Total Synthesis on Chemistry, Biology and Medicine

“…Our first total synthesis delivered the natural substance in racemic form and allowed its full relative stereochemical assignment, while our second and asymmetric synthesis delivered its natural enantiomeric form and proved its absolute configuration . In our most recent total synthesis of uncialamycin we discovered and employed a much more efficient method for the construction of its anthraquinone moiety and developed a streamlined process for its production (22 linear steps, 11 % overall yield) . Summarized in Figure [from building blocks J – N and intermediates (+)‐ 74 –(+)‐ 77 ], this strategy was employed for the construction of numerous analogues of uncialamycin, some with low picomolar potencies against a variety of tumor cells.…”

Wolf‐Preis in Chemie: K. C. Nicolaou und S. L. Schreiber / Preise der Israel Chemical Society: R. Klajn, R. Tenne und M. Kol / Pittcon‐2016‐Preise: S. A. Asher, D. R. Walt, J. Popp, S. Mukamel und R. J. White

“…Nicolaou ist zudem der Autor, von dem die meisten Veröffentlichungen in der Angewandten Chemie erschienen sind. Vor kurzem hat er hier die Synthese substituierter amino‐ und methoxyphenolischer Anthrachinone vorgestellt und in ChemMedChem Epothilonanaloga . Nicolaou ist Mitglied der Boards von Chemistry—An Asian Journal , Chemistry—A European Journal und ChemistryOpen und gehörte 1995–2013 dem Internationalen Beirat der Angewandten Chemie an.…”