Synthesis 2018; 50(06): 1301-1306
DOI: 10.1055/s-0036-1591866
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Total Synthesis of (+)-Coprophilin

Isamu Shiina*
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan   Email: shiina@rs.kagu.tus.ac.jp
,
Yuma Umezaki
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan   Email: shiina@rs.kagu.tus.ac.jp
,
Takatsugu Murata
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan   Email: shiina@rs.kagu.tus.ac.jp
,
Kyohei Suzuki
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan   Email: shiina@rs.kagu.tus.ac.jp
,
Takayuki Tonoi
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan   Email: shiina@rs.kagu.tus.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 13 October 2017

Accepted after revision: 21 November 2017

Publication Date:
21 December 2017 (online)


Abstract

In this paper, we report the first total synthesis of (+)-coprophilin, an anticoccidial agent, by constructing the chiral linear precursor via a Mukaiyama–Evans aldol reaction and a stereoselective intramolecular Diels–Alder reaction. The proposed method can be used to provide large amounts of (+)-coprophilin, which exhibits a 3,4,5,6,7-pentasubstituted Δ1,2-octalin core structure.

Supporting Information

 
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