89877-54-3Relevant academic research and scientific papers
Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B
Uesugi, Shun-Ichiro,Watanabe, Tsubasa,Imaizumi, Takamichi,Ota, Yu,Yoshida, Keisuke,Ebisu, Haruna,Chinen, Takumi,Nagumo, Yoko,Shibuya, Masatoshi,Kanoh, Naoki,Usui, Takeo,Iwabuchi, Yoshiharu
, p. 12333 - 12350 (2016/01/09)
Irciniastatin A (a.k.a. psymberin) and irciniastatin B are members of the pederin natural product family, which have potent antitumor activity and structural complexity. Herein, we describe a full account of our total synthesis of (+)-irciniastatin A and (-)-irciniastatin B. Our synthesis features the highly regioselective Eu(OTf)3-catalyzed, DTBMP-assisted epoxide ring opening reaction with MeOH, which enabled a concise synthesis of the C1-C6 fragment, extensive use of AZADO (2-azaadamantane N-oxyl) and its related nitroxyl radical/oxoammonium salt-catalyzed alcohol oxidation throughout the synthesis, and a late-stage assembly of C1-C6, C8-C16, and C17-C25 fragments. In addition, for the synthesis of (-)-irciniastatin B, we achieved the C11-selective control of the oxidation stage via regioselective deprotection and AZADO-catalyzed alcohol oxidation. The synthetic irciniastatins showed high levels of cytotoxic activity against mammalian cells. Furthermore, chemical footprinting experiments using synthetic compounds revealed that the binding site of irciniastatins is the E-site of the ribosome.
Synthesis of 8-desmethoxy psymberin: A putative biosynthetic intermediate towards the marine polyketide psymberin
Bielitza, Max,Pietruszka, J?rg
supporting information, p. 8300 - 8308 (2013/07/25)
The synthesis of a putative biosynthetic precursor of psymberin including a formal synthesis of the natural product is described. The key step towards the densely functionalized tetrahydropyran core was an enantioselective catalytic Mukaiyama aldol reacti
Trimethoxyphenyl Compounds, XI. Constituents of Hagenia abyssinica, 2: Synthesis of Phloracylophenones Containing One Phloroglucinol Unit
Schiemenz, Guenter Paulus,Behrens, Heinz,Ebert, Claus Peter,Maienschein, Konrad,Schroeder, Jens-Michael
, p. 681 - 692 (2007/10/02)
For the Koso constituents K6 and K8, we previously proposed the structures 1a, b and 2a, b.These assignments have been confirmed by synthesis. - Keywords: Flores koso, Revised Structure, Synthesis of Phloroglucinols
Trimethoxyphenyl Compounds, X. Constituents of Hagenia abyssinica, 1: Isolation of Kosins and Structure Elucidation of Phloracylophenones Containing One Phloroglucinol Unit
Schiemenz, Guenter Paulus,Schroeder, Jens-Michael
, p. 669 - 680 (2007/10/02)
From Hagenia abyssinica, 26 compounds were isolated, mostly phloracylophenones with one to three phloroglucinol units.The structure elucidation of three phloracylophenones with one phloroglucinol unit is described. - Keywords: Flores koso, Natural Phlorog
