Synthesis 2015; 47(09): 1348-1355
DOI: 10.1055/s-0034-1379898
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (+)-Clavulatriene A

Fumihiro Ito
a  Graduate 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
a  Graduate 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
a  Graduate 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
a  Graduate 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
a  Graduate 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
b  Kitasato 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
b  Kitasato 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*
a  Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan   Email: nagamitsut@pharm.kitasato-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 13 January 2015

Accepted after revision: 02 February 2015

Publication Date:
05 March 2015 (eFirst)

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.

Supporting Information

 
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