Mar. Drugs 2012, 10(4), 881-889; doi:10.3390/md10040881
Communication

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

Jianyun Sunemail, Yanhui Douemail, Haixin Dingemail, Ruchun Yangemail, Qi Sunemail and Qiang Xiao* email
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang 330013, China
* Author to whom correspondence should be addressed.
Received: 29 January 2012; in revised form: 16 March 2012 / Accepted: 24 March 2012 / Published: 10 April 2012
PDF Full-text Download PDF Full-Text [642 KB, uploaded 10 April 2012 14:48 CEST]
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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

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.

Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert