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Synthesis 2002(1): 0001-0028
DOI: 10.1055/s-2002-19289
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-branched Sugars

Eiko Ichikawaa,, Kuniki Kato*b
a Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Yokohama 223-8522, Japan
b Research Laboratories, Pharmaceutical Group, Nippon Kayaku Co. Ltd, Shimo, Kita-ku, Tokyo 115-8588, Japan
e-Mail: ki-kato@spn1.speednet.ne.jp;
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Publikationsverlauf

Received 5 September 2001
Publikationsdatum:
04. August 2004 (online)

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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

1

Current address: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.