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Open AccessCommunication
Mar. Drugs 2019, 17(4), 226; https://doi.org/10.3390/md17040226

Total Synthesis of Mycalisine B

Jiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China
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Received: 18 March 2019 / Revised: 9 April 2019 / Accepted: 10 April 2019 / Published: 14 April 2019
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Abstract

The first total synthesis of the marine nucleoside Mycalisine B—a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside—has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-O-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) I2 catalyzed acetonide formation from 1,2,3,5-tetra-O-acetylribose and acetone at large scale; (2) Vorbrüggen glycosylation using N4-benzoyl-5-cyano-6-bromo-7H-pyrrolo[2,3–d]pyrimidine as a nucleobase to avoid formation of N-3 isomer; (3) mild and scalable reaction conditions. View Full-Text
Keywords: marine nucleoside; total synthesis; vorbrüggen glycosylation; mycalisine B marine nucleoside; total synthesis; vorbrüggen glycosylation; mycalisine B
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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 (CC BY 4.0).

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Ding, H.; Ruan, Z.; Kou, P.; Dong, X.; Bai, J.; Xiao, Q. Total Synthesis of Mycalisine B. Mar. Drugs 2019, 17, 226.

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