First synthesis of 4′-selenonucleosides showing unusual southern conformation

Shin Jeong Lak, Dilip K. Tosh, Ok Kim Hea, Ting Wang, Xiyan Hou, Seop Yun Ho, Youngjoo Kwon, Kook Lee Sang, Jungwon Choi, Xuan Zhao Long

Research output: Contribution to journalArticlepeer-review

68 Scopus citations

Abstract

(Chemical Equation Presented) The first synthesis of 4′- selenonucleosides was achieved using a Pummerer-type condensation as a key step. All stereoelectronic effects shown in 4′-oxonucleosides were overwhelmed by the size of selenium and steric interactions, driving the conformation to the C2′-endo/C3′-exo twist (Southern) conformation.

Original languageEnglish
Pages (from-to)209-212
Number of pages4
JournalOrganic Letters
Volume10
Issue number2
DOIs
StatePublished - 17 Jan 2008

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