Total Synthesis of (+)-Clavulatriene A

Fumihiro Ito; Yuki Ohbatake; Satoshi Aoyama; Tatsuya Ikeda; Shiho Arima; Yuuki Yamada; Haruo Ikeda; Tohru Nagamitsu

doi:10.1055/s-0034-1379898

Synthesis, Table of Contents

Synthesis 2015; 47(09): 1348-1355
DOI: 10.1055/s-0034-1379898

paper

Total Synthesis of (+)-Clavulatriene A

Fumihiro Ito

^aGraduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan Email: nagamitsut@pharm.kitasato-u.ac.jp

,

Yuki Ohbatake

^aGraduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan Email: nagamitsut@pharm.kitasato-u.ac.jp

,

Satoshi Aoyama

^aGraduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan Email: nagamitsut@pharm.kitasato-u.ac.jp

,

Tatsuya Ikeda

^aGraduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan Email: nagamitsut@pharm.kitasato-u.ac.jp

,

Shiho Arima

^aGraduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan Email: nagamitsut@pharm.kitasato-u.ac.jp

,

Yuuki Yamada

^bKitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan

,

Haruo Ikeda

^bKitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan

,

Tohru Nagamitsu*

^aGraduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan Email: nagamitsut@pharm.kitasato-u.ac.jp

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Abstract

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Abstract

The protecting-group-free total synthesis of (+)-clavulatriene A has been achieved. Key features of the synthetic strategy include the development of a novel strategy for the practical synthesis of α-cyperone, and a one-pot palladium-catalyzed reductive desulfonylation and deacetoxylation reaction. Furthermore, the total synthesis described in this study allowed for the determination of the absolute configuration of (+)-clavulatriene A.

Key words

protecting-group-free - total synthesis - clavulatriene A - absolute configuration

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References

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