通过四丁基氟化铵促进吲哚环形成简洁合成呋甾替林。

A concise synthesis of furostifoline by tetrabutylammonium fluoride-promoted indole ring formation.

作者信息

Yasuhara Akito, Suzuki Naoyuki, Sakamoto Takao

机构信息

Graduate School of Pharmaceutical Sciences, Tohoku University Aobaku, Sendai, Japan.

出版信息

Chem Pharm Bull (Tokyo). 2002 Jan;50(1):143-5. doi: 10.1248/cpb.50.143.

DOI:10.1248/cpb.50.143

PMID:11824578

Abstract

Furostifoline, a furo[3,2-a]carbazole alkaloid, was synthesized in 10% overall yield in four steps from 2-acetyl-3-bromofuran. The key step of this synthesis was the 2-substituted indole formation with tetrabutylammonium fluoride (TBAF) from 2-(2-propenyl)-3-((2-ethoxycarbonylamino)phenylethynyl)furan, which was easily prepared from ethyl 2-ethynylphenylcarbamate with 3-bromo-2-(2-propenyl)furan by the Sonogashira reaction.

摘要

呋甾替林，一种呋喃并[3,2-a]咔唑生物碱，以2-乙酰基-3-溴呋喃为原料，经四步反应合成，总产率为10%。该合成的关键步骤是由2-(2-丙烯基)-3-((2-乙氧基羰基氨基)苯乙炔基)呋喃与四丁基氟化铵(TBAF)形成2-取代吲哚，2-(2-丙烯基)-3-((2-乙氧基羰基氨基)苯乙炔基)呋喃可由2-乙炔基苯基氨基甲酸乙酯与3-溴-2-(2-丙烯基)呋喃通过Sonogashira反应轻松制备。