期刊
MARINE DRUGS
卷 17, 期 4, 页码 -出版社
MDPI
DOI: 10.3390/md17040226
关键词
marine nucleoside; total synthesis; vorbruggen glycosylation; mycalisine B
资金
- National Natural Science Foundation of China [21676131, 21462019]
- Science Foundation of Jiangxi Province [20143ACB20012]
- Jiangxi Science & Technology Normal University [2018BSQD022]
The first total synthesis of the marine nucleoside Mycalisine Ba naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleosidehas 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) I-2 catalyzed acetonide formation from 1,2,3,5-tetra-O-acetylribose and acetone at large scale; (2) Vorbruggen glycosylation using N-4-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.
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