Efficient Synthesis of (–)-Hanishin, (–)-Longamide B, and (–)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

Koichi Fukase, Yukari Fujimoto, Zenyu Shiokawa, Shinsuke Inuki

doi:10.1055/s-0035-1560988

Efficient Synthesis of (–)-Hanishin, (–)-Longamide B, and (–)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

Koichi Fukase

Department of Chemistry, Graduate School of Science, Osaka University
Yukari Fujimoto

Department of Chemistry, Faculty of Science and Technology, Keio University
Zenyu Shiokawa

Department of Chemistry, Graduate School of Science, Osaka University
Shinsuke Inuki

Department of Chemistry, Faculty of Science and Technology, Keio University

説明

We describe a simple chiral-pool synthesis of (–)-longamide B, (–)-longamide B methyl ester, and (–)-hanishin. The key feature of the total synthesis is the formation of a piperazinone from a 1,2-cyclic sulfamidate and methyl 2-pyrrolecarboxylate, which permits efficient construction of the pyrrolopiperazinone core scaffold.

Efficient Synthesis of (–)-Hanishin, (–)-Longamide B, and (–)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

説明

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問題の指摘

Efficient Synthesis of (–)-Hanishin, (–)-Longamide B, and (–)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

説明

収録刊行物

被引用文献 (1)*注記

関連プロジェクト

詳細情報 詳細情報について

書き出し

問題の指摘

詳細情報詳細情報について