164672-56-4Relevant articles and documents
A versatile total synthesis of trachycladines A and B and their analogues
Peitsinis, Zisis V.,Melidou, Dafni A.,Stefanakis, John G.,Evgenidou, Helen,Koumbis, Alexandros E.
, p. 8160 - 8166 (2014)
The synthesis of marine nucleosides trachycladines A and B and two nucleoside analogues was accomplished following a versatile and high-yielding scheme starting from D-ribose. The key step involved a regio-and stereoselective direct Vorbrüggen glycosylati
Concise total synthesis of two marine natural nucleosides: Trachycladines A and B
Ding, Haixin,Li, Wei,Ruan, Zhizhong,Yang, Ruchun,Mao, Zhijie,Xiao, Qiang,Wu, Jun
supporting information, p. 1681 - 1685 (2014/08/18)
We report the first total synthesis of trachycladines A (10 steps, 34.2% overall yield) and B (11 steps, 35.0% overall yield) by using 5-deoxy-1,2,3-tri-O-acetyl-β-D-ribofuranose as the starting material. The critical step was the SnCl4 assisted regio- and steroselective deprotection of perbenzylated 1-O-methyl-5-deoxyribofuranose. The enzyme adenylate deaminase (EC 3.5.4.6) was successfully applied to the chemoenzymatic synthesis of trachycladines B.
Asymmetric synthesis of 4′-epi-trachycladines A and B
Enders, Dieter,Breuer, Irene,Drosdow, Eugen
, p. 3239 - 3244 (2007/10/03)
The first asymmetric synthesis of 4′-epi-trachycladines A and B is reported. Starting from 2,2-dimethyl-1,3-dioxan-5-one the title nucleosides were synthesised in 14 steps employing the SAMP-/RAMP-hydrazone methodology. The dioxanone-SAMP-hydrazone was first transformed into a trisubstituted derivative by a triple α-/α′-alkylation. Removal of the chiral auxiliary and subsequent reduction gave the corresponding alcohol, which could be transformed over four steps into TBS-protected 2′-C-methyl-5′-deoxy- L-lyxose. The trachycladines were then obtained via the corresponding triacetate using standard Vorbrueggen and silyl-Hilbert-Johnson conditions in an overall yield of 18-21%. Such 2′-C-branched ribonucleosides are potential agonists for adenosine receptors and play an important role in drug discovery. Georg Thieme Verlag Stuttgart.
