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Dedication to Kyoichi A. Watanabe

This issue of Heterocyclic Communications is dedicated to Kyoichi A. ‘Kyo’ Watanabe (1935–2015), formerly of the Memorial Sloan Kettering Cancer Center (MSKCC), Codon Pharmaceuticals and Pharmasset, Inc. Kyo earned his PhD in the Mizuno lab at Hokkaido University. He was a member of the American Chemical Society, the Polish Academy of Sciences and a founding member of the International Society of Nucleosides, Nucleotides and Nucleic Acids (IS3NA). As the head of the Organic Chemistry Laboratory at MSKCC and Vice President for Research and Development at Pharmasset he was an eminent organic chemist who trained and influenced the careers of numerous scientists. Kyo’s impact has been recognized in five international awards, the most notable and recent being the Marie Skłodowska-Curie medal (1993), the František Šorm medal (2003), and a Lifetime Achievement award from the IS3NA (2015). Obituaries were published by the IS3NA (http:// www.is3na.org/IS3NA_News_Details.asp?id=54) and The Atlanta Journal-Constitution, April 12, 2015. Kyo’s academic career began at Hokkaido University in Japan where he earned his MS (1960). He then completed his PhD thesis in the Mizuno lab at Hokkaido in 3 years. From there Kyo joined Jack Fox’s group at MSKCC, left briefly for a fellowship in the Lemieux laboratory at the University of Alberta [1–3], and returned to Sloan-Kettering where he steadily advanced to become the head of the MSKCC laboratory of organic chemistry. While at Sloan-Kettering, Kyo held a professorship at Cornell University until his retirement from academia in 1996. After leaving MSKCC, Kyo joined Codon Pharmaceuticals as the Director of Chemistry. He joined Pharmasset in 1998 where he was the Vice President for Research and Development until he retired in 2003. Throughout his career Kyo was strongly influenced by pioneers in chemistry such as Liebig, Miescher, and Fischer [4]. The elucidation of the structures of the Aand B-form DNA helixes by Watson and Crick also had a profound influence [4]. Kyo was best known for synthesis of novel nucleosides, antivirals, anti-cancer agents, total synthesis of natural products, and carbohydrate ring transformations. He was the first to synthesize the natural products gougerotin and the blasticidins [5–8]. He was also the first to synthesize a 2-fluoro-2-deoxy-D-arabinose derivative from D-glucose [9]. The above arabinose was key in synthesis of Faranucleosides that have anti-viral activity [10–13], anti-cancer activity [14–16] and are commercially available today. Important examples of these nucleosides include 1-(2′-deoxy-2′fluoro-1-β-D-arabinofuranosyl)-5-methyluracil (FMAU) and 1-(2-deoxy-2-fluoro-1-β-D-arabinofuranosyl)-5-iodouracil (FIAU, fialuridine). FMAU advanced to clinical trials for cancer [17] and a radiolabeled FMAU has been used as an imaging agent [18]. FIAU reached clinical trials for hepatitis B but was withdrawn due to safety concerns [19]. However, the most notable example is probably 2′-F-ara-C. Radiolabeled versions are used in positron emission tomography imaging and for in vivo prediction of clinical response to gemcitabine [20].