Total Synthesis of Mycalisine B
AbstractThe 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
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Ding, H.; Ruan, Z.; Kou, P.; Dong, X.; Bai, J.; Xiao, Q. Total Synthesis of Mycalisine B. Mar. Drugs 2019, 17, 226.
Ding H, Ruan Z, Kou P, Dong X, Bai J, Xiao Q. Total Synthesis of Mycalisine B. Marine Drugs. 2019; 17(4):226.Chicago/Turabian Style
Ding, Haixin; Ruan, Zhizhong; Kou, Peihao; Dong, Xiangyou; Bai, Jiang; Xiao, Qiang. 2019. "Total Synthesis of Mycalisine B." Mar. Drugs 17, no. 4: 226.
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