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

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

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China
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Received: 29 January 2012 / Revised: 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 (CC BY 3.0).

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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.

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