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.
journal_name
Mar Drugsjournal_title
Marine drugsauthors
Ding H,Ruan Z,Kou P,Dong X,Bai J,Xiao Qdoi
10.3390/md17040226subject
Has Abstractpub_date
2019-04-14 00:00:00issue
4issn
1660-3397pii
md17040226journal_volume
17pub_type
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