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Open AccessCommunication

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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Mar. Drugs 2019, 17(4), 226; https://doi.org/10.3390/md17040226
Received: 18 March 2019 / Revised: 9 April 2019 / Accepted: 10 April 2019 / Published: 14 April 2019
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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MDPI and ACS Style

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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