Concise total synthesis of two marine natural nucleosides: trachycladines A and B

• Haixin Ding,
• Wei Li,
• Zhizhong Ruan,
• Ruchun Yang,
• Zhijie Mao,
• Qiang Xiao and
• Jun Wu

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: marine nucleosides; natural products; total synthesis; trachycladines A and B; Vorbrüggen glycosylation; Introduction Marine

• (Ara-A) [11], and azidothymidine (AZT) [12] for clinical use. As a key class of marine natural nucleosides, trachycladines A and B (Figure 1) hold an important position in drug development. Both trachycladines A and B contain a rare naturally occurring 2′-C-methyl-5′-deoxy-D-ribose sugar moiety. The

• chemical structure for the first time. Results and Discussion Until now, there is only one publication about the total synthesis of analogues of trachycladines A and B. In 2005, Enders et al. reported the first asymmetric synthesis of 4′-epi-trachycladines A and B in 14 steps. They used 2,2-dimethyl-1,3