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Short‐Step Anodic Access to Emissive RNA Homonucleosides (Eur. J. Org. Chem. 7/2014)
Author(s) -
Okada Yohei,
Shimada Kouhei,
Kitano Yoshikazu,
Chiba Kazuhiro
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201490015
Subject(s) - chemistry , yield (engineering) , lithium perchlorate , nitromethane , nucleophile , lithium (medication) , combinatorial chemistry , anode , anthracene , photochemistry , electrolyte , organic chemistry , electrode , catalysis , medicine , materials science , metallurgy , endocrinology
The cover picture shows a schematic impression of our synthetic approach toward new emissive nucleoside analogues. Our methodology employs an anodic oxidation of methoxyphenols (right) in lithium perchlorate/nitromethane electrolyte solution, generating reactive phenoxonium ions, which were then trapped by nucleophilic allyl ribose (left) to construct emissive base analogues in one step from non‐emissive starting materials. The straight one‐way road represents a short‐step synthesis, and allyl ribose should “yield” the right‐of‐way to methoxyphenols to “yield” the desired products. Details are discussed in the Short Communication by K. Chiba et al. on p. 1371 ff.