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Mass Spectrometry-Based Metabolomics to Elucidate Functions in Marine Organisms and Ecosystems
Mar. Drugs 2012, 10(4), 881-889; doi:10.3390/md10040881
Communication

First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside

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Received: 29 January 2012; in revised form: 16 March 2012 / Accepted: 24 March 2012 / Published: 10 April 2012
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Abstract: 4-Amino-7-(5′-deoxy-β-d-xylofuranosyl)-5-iodo-pyrrolo[2,3-d]pyrimidine 1, an unusual naturally occurring marine nucleoside isolated from an ascidan, Diplosoma sp., was synthesized from d-xylose in seven steps with 28% overall yield on 10 g scale. The key step was Vorbrüggen glycosylation of 5-iodo-pyrrolo[2,3-d]pyrimidine with 5-deoxy-1, 2-O-diacetyl-3-O-benzoyl-d-xylofuranose. Its absolute configuration was confirmed.
Keywords: Vorbrüggen glycosylation; total synthesis; pyrrolo[2,3-d]pyrimidine; marine nucleoside Vorbrüggen glycosylation; total synthesis; pyrrolo[2,3-d]pyrimidine; marine nucleoside
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Sun, J.; Dou, Y.; Ding, H.; Yang, R.; Sun, Q.; Xiao, Q. First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside. Mar. Drugs 2012, 10, 881-889.

AMA Style

Sun J, Dou Y, Ding H, Yang R, Sun Q, Xiao Q. First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside. Marine Drugs. 2012; 10(4):881-889.

Chicago/Turabian Style

Sun, Jianyun; Dou, Yanhui; Ding, Haixin; Yang, Ruchun; Sun, Qi; Xiao, Qiang. 2012. "First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside." Mar. Drugs 10, no. 4: 881-889.


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