Abstract
Since the naturally occurring unusual nucleoside oxetanocin A and its derivatives
have been found to be effective as anti-HIV-1 and anti-herpes virus agents in 1986,
the syntheses of different types of sugar-modified nucleoside analogs have been reported.
In this review we will give an overview of the efforts to synthesize oxetanocin A
from the first synthesis in 1987 and the related unusual nucleosides with bis(hydroxymethyl)-branched
sugars, including our works in this area.
1 Introduction
2 Total Synthesis of Oxetanocin A
2.1 Nippon Kayaku’s Synthesis
2.2 Abbott’s Synthesis
2.3 Yamamura’s Synthesis
2.4 Fleet’s Synthesis
2.5 Just’s Synthesis
3 Practical Synthesis of 1-O -Acetyloxetanose Derivatives
4 Chemical Reactivity and Transformation of OXT-A
4.1 Enzymatic Transformation of OXT-A
4.2 Chemical Reactivity of OXT-A
4.3 Alkylphosphonic Acid Derivatives of OXT-A
5 Oxetanosyl C -Nucleosides
5.1 Re-examination of Ring Transformation
5.2 Synthesis of C -Oxetanosyl Nucleosides
5.2.1 Synthesis of C -Oxetanosyl Maleimide
5.2.2 Synthesis of C -Oxetanosyl Thiazole
6 Carbocyclic Analogs of OXT-A
6.1 Honjo’s Synthesis
6.2 Narasaka’s Synthesis
6.3 Squibb’s Synthesis
6.4 Abbott’s Synthesis (I)
6.5 Kaneko’s Synthesis
6.6 Abbott’ Synthesis (II)
6.7 Bristol-Meyers-Squibb’s Synthesis
6.8 Robert’s Synthesis
6.9 Kato’s Synthesis
6.10 Jung’s Synthesis
6.11 Taguchi’s Synthesis
6.12 Somekawa’s Synthesis
6.13 Hegedus’ Synthesis
7 Thietanosyl Nucleosides
8 Azetidinyl Nucleosides
9 Nucleosides with Bis(hydroxymethyl)-branched Sugars
9.1 Cyclopropyl Carbocyclic Nucleosides
9.2 Ring-enlarged OXT-A Analogs
9.3 Ring-enlarged COXT-A Analogs
9.4 4"-Thionucleoside Analogs
9.5 Miscellaneous
10 Conclusions
Key words
nucleobases - nucleosides - glycosidation - heterocycles - total synthesis
