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Nucleosides, Nucleotides & Nucleic Acids Volume 25, 2006 - Issue 4-6
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Original Articles

Improved Industrial Syntheses of Penciclovir and Famciclovir Using N2-Acetyl-7-Benzylguanine and a Cyclic Side Chain Precursor

Takayoshi Torii Amino Science Laboratories, Ajinomoto Co., Inc., Kawasaki-ku, Kawasaki, Japan
,
Keizo Yamashita Amino Science Laboratories, Ajinomoto Co., Inc., Kawasaki-ku, Kawasaki, Japan
,
Mitsuhiko Kojima Amino Science Laboratories, Ajinomoto Co., Inc., Kawasaki-ku, Kawasaki, Japan
,
Yumiko Suzuki Amino Science Laboratories, Ajinomoto Co., Inc., Kawasaki-ku, Kawasaki, Japan
,
Toyoto Hijiya Amino Science Laboratories, Ajinomoto Co., Inc., Kawasaki-ku, Kawasaki, Japan
&
Kunisuke Izawa Amino Science Laboratories, Ajinomoto Co., Inc., Kawasaki-ku, Kawasaki, Japan
Pages 625-634 | Received 19 Jan 2006, Accepted 21 Feb 2006, Published online: 07 Feb 2007
 
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We have established practical synthetic methods for penciclovir (PCV, 1) and famciclovir (FCV, 2) from N2-acetyl-7-benzylguanine (NAc7BnG, 3) and 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (4)—the latter being a more easily prepared cyclic precursor of the diacetate side chain (5) used in the conventional process. The coupling of 4 with 3 proceeded regioselectively at the N9 position of guanine in good yield. The coupling product was then successfully transformed into the known antiviral agents in a short number of steps.

Acknowledgments

This article is dedicated to Professor Eiko Ohtsuka on the occasion of her 70th birthday.

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