The first total synthesis of mycalisine A, a pyrrolo[2,3-dlpyrimidine nucleoside, was accomplished by a multi-step synthesis from toyocamycin.
A novel and efficient synthesis of the naturally occurring nucleoside doridosine
β Scribed by Ji-Wang Chern; Leroy B. Townsend
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 264 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
1-Methylisoguanosine was synthesized by a one-pot reaction involving a condensation of 5-amino-l-(L3-D-ribofuranosyl)imidazole-4-carboxamide (1) with methyl isothiocyanate, treatment of the resulting thiourea derivative with DCC furnished 5-(3-methyl-1-ureidol-l-(&gribofuranosyl)imidazole-4-carbonitrile ($1 which was then annulated with ethanolic ammonia to furnish doridosine in a 68% yield from 1. l-Methylisoguanosine (2, doridosine. 6-amino-l-methy1-9-fi-~-ribofuranosylpurin-2-one) was recently isolated from three different marine animals by three independent laboratories. 2-4 This compound has been shown to possess potent muscle-relaxant activity, as well as a lowering
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