27267-71-6Relevant articles and documents
A convergent total synthesis of the telomerase inhibitor (±)-γ-rubromycin
Wilsdorf, Michael,Reissig, Hans-Ulrich
, p. 4332 - 4336 (2014/05/06)
The total synthesis of the human telomerase inhibitor γ-rubromycin in its racemic form was accomplished in 3.8 % overall yield. The key feature of this synthesis is an efficient acid-catalyzed spiroketalization for the construction of the spiroketal core. The required electronically well-balanced spiroketal precursor was obtained by the convergent assembly of a naphthyl-substituted aldehyde, an α-methoxyallyl-γ-silyl-substituted phosphonate as the central C3 building block, and a highly functionalized aryl Grignard reagent. Another key feature is the late-stage construction of the isocoumarin moiety and a simultaneous protodesilylation furnishing the known methyl aryl ether protected precursor of γ-rubromycin. 3 building blocks + 3 acids→natural product: After the assembly of the crucial precursor from three highly functionalized building blocks, the pivotal spiroketalization was achieved with trifluoromethanesulfonic acid, the isocoumarin formation with fluoroboric acid, and the O-demethylation with the Lewis acid boron tribromide. (±)-γ-Rubromycin was thus synthesized in 18 steps with an overall yield of 3.8 % from commercially available precursors.
Total synthesis of (±)-γ-rubromycin on the basis of two aromatic pummerer-type reactions
Akai, Shuji,Kakiguchi, Keisuke,Nakamura, Yuka,Kuriwaki, Ikumi,Dohi, Toshifumi,Harada, Shusaku,Kubo, Ozora,Morita, Nobuyoshi,Kita, Yasuyuki
, p. 7458 - 7461 (2008/09/18)
(Chemical Equation Presented) Double or nothing: In a convergent synthesis of the title compound, a potent inhibitor of human telomerase, two different aromatic Pummerer-type reactions were employed to construct the pivotal bisbenzannelated spiroketal ske
