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Carbocyclic analogs of nucleosides. Part 2. . Synthesis of 2′,3′‐dideoxy‐5′‐homonucleoside analogs
Author(s) -
Jenny Thomas F.,
Horlacher Jennifer,
Previsani Nicoletta,
Benner Steven A.
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750620
Subject(s) - chemistry , nucleoside , stereochemistry , mitsunobu reaction , nucleoside analogue , purine metabolism , base (topology) , molecule , scope (computer science) , combinatorial chemistry , organic chemistry , mathematical analysis , mathematics , computer science , programming language , enzyme
A set of derivatives of cyclopentaneacetic acid cis ‐substituted at position 3 by nucleoside bases (both purines and pyrimidines) were prepared and characterized (see 11, 14 , and 23a, b; Schemes 2–4 ). These molecules are carbocyclic analogs of 2′,3′‐dideoxy‐5′‐homonucleosides. In this synthesis, the skeleton was constructed from norbornanone and a novel method based on Mitsunobu chemistry used for the introduction of nucleoside‐base substituents. The scope of this method was further explored via the preparation of a cyclobutyl analog of dideoxyguanosine (see 17 , Scheme 3 ).