- Total synthesis of mycalisine B
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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.
- Ding, Haixin,Ruan, Zhizhong,Kou, Peihao,Dong, Xiangyou,Bai, Jiang,Xiao, Qiang
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- CYCLIC DI-NUCLEOTIDE COMPOUNDS AND METHODS OF USE
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Disclosed are cyclic-di-nucleotide cGAMP analogs, methods of synthesizing the compounds, pharmaceutical compositions comprising the compounds thereof, and use of compounds and compositions in medical therapy.
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Paragraph 0235
(2017/10/11)
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- A total synthesis of mycalisine A
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In this paper, we report a total synthesis of a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside, mycalisine A. Our synthetic strategy uses d-xylose as the starting material and Vorbrüggen glycosylation as the key step. Mycalisine A was synthesized in 11 steps with a 15% overall yield.
- Dou, Yan-Hui,Ding, Hai-Xin,Yang, Ru-Chun,Li, Wei,Xiao, Qiang
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p. 379 - 382
(2013/07/04)
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