Synthesis of Renieramycins: Construction of the Core Ring System of Cribrostatin 4 through Modified Pictet–Spengler Cyclization of 3,6-Bisarylpiperazine-2,5-dione with Diethoxyethyl Benzoate

Masashi Yokoya; Hiroshi Ito; Naoki Saito

doi:10.1248/cpb.59.787

Notes

Synthesis of Renieramycins: Construction of the Core Ring System of Cribrostatin 4 through Modified Pictet–Spengler Cyclization of 3,6-Bisarylpiperazine-2,5-dione with Diethoxyethyl Benzoate

Masashi Yokoya, Hiroshi Ito, Naoki Saito

著者情報

キーワード: cribrostatin 4, marine natural product, Pictet–Spengler cyclization, tetrahydroisoquinoline, preparation

ジャーナルフリー

2011 年 59 巻 6 号 p. 787-792

DOI https://doi.org/10.1248/cpb.59.787

詳細

抄録

A nine-step synthesis of pentacyclic key intermediate 11 of cribrostatin 4 (2) along with renieramycin I (1i) from 3,6-bisarylpiperazine-2,5-dione derivative 3 is described. The key step of this synthesis is the stereoselective cyclization of lactam nitrogen with diethoxyethyl benzoate, followed by the stereoselective hydrogenation to generate ABC ring system 6.

責任著者(Corresponding author)

J-STAGEへの登録はこちら（無料）