Beilstein J. Org. Chem.2017,13, 855–862, doi:10.3762/bjoc.13.86
number of antiviral and antitumor drugs [3][4]. On the other hand, naturally occurring nucleosides, especially marinenucleosides, have also played an indispensable role in drug discovery, which make great contribution in the commercialization of cytosine arabinoside (Ara-C), adenine arabinoside (Ara-A
) and AZT, etc. [5][6]. Nucleosides and their analogues will continue to play an important role in future drug discovery [7].
In the past decades, exploration of novel naturally occurring marinenucleosides has made expeditious achievements [8][9][10]. Some of them showed promising antibiotic, antiviral
studies of marinenucleosides, total syntheses of several marinenucleosides were accomplished in our group [14][15][16][17][18]. In the present paper, we reported a practical approach for the total synthesis of kipukasin A.
Results and Discussion
From the synthetic point of view, it seemed that the most
Beilstein J. Org. Chem.2014,10, 1681–1685, doi:10.3762/bjoc.10.176
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.
Keywords: marinenucleosides; natural products; total synthesis; trachycladines A and B; Vorbrüggen glycosylation; Introduction
Marine
]. The initial discovery of marinenucleosides can be traced back to the identifications of spongothymidine and spongouridine in the early 1950s from the Caribbean sponge Tethyacrypta [8][9], which subsqeuently led to the commercialization of arabinofuranosylcytosine (Ara-C) [10], arabinofuranosyladenine
kinase receptors and play an important role in related drug discovery [15].
To facilitate the discovery of lead compounds as anticancer reagents from marinenucleosides [16][17][18], the total synthesis of trachycladines A and trachycladines B are reported herein allowing to assemble their unique