Synthesis of the Fluoromethyl Derivatives of Carbocyclic Oxetanocin A |
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| Authors: | Yoshiko Sato Kenji Ueyama Tokumi Maruyama Douglas D Richman |
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| Institution: | 1. Department of Pharmaceutical Sciences , Tokushima Brnri University , Yamashiro-cho, Tokushima , 770 , JAPAN;2. Departments of Pathology and Medicine , University of California , San Diego, La Jolla , California , 92093-0679 , U. S. A. |
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| Abstract: | Abstract Treatment of the 2,3-di-O-benzoate 1 with sodium boronhydride mainly afforded the 3-O-benzoate 2 accompanied with isomers 3a,b and fully deprotected product 4. Compound 2 was converted to 5, from which 8 was obtained. The 1-cyclobutanols 8 and 5 were successfully condensed with 6-chloropurine by Mitsunobu reaction to give 9 and 11, respectively. After partial deprotection, the cyclobutyl nucleosides 10 and 15 were subjected to fluorination using DAST to afford the fluoromethyl analogs 12 and 16 from which target compounds 14 and 17 were obtained in good yields, respectively. |
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