Next Article in Journal
The Ameliorating Effect of Plasma Protein from Tachypleus tridentatus on Cyclophosphamide-Induced Acute Kidney Injury in Mice
Previous Article in Journal
Protective Effect of Phloroglucinol on Oxidative Stress-Induced DNA Damage and Apoptosis through Activation of the Nrf2/HO-1 Signaling Pathway in HaCaT Human Keratinocytes
Article Menu
Issue 4 (April) cover image

Export Article

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
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(4), 226;
Received: 18 March 2019 / Revised: 9 April 2019 / Accepted: 10 April 2019 / Published: 14 April 2019
PDF [1242 KB, uploaded 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

Graphical abstract

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).

Supplementary material


Share & Cite This Article

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top