Synthesis of the oxindole alkaloid (−)-horsfiline

Q2 Chemistry Tetrahedron, asymmetry Pub Date : 1994-10-01 DOI:10.1016/S0957-4166(00)86273-4

Claudio Pellegrini, Christoph Strässler, Michael Weber, Hans-Jürg Borschberg ∗

引用次数: 62

Abstract

A synthesis of (-)-horsfiline ((-)-1), a metabolite isolated recently from Horsfieldia superba, is described. The diastereoface selectivity of the crucial oxidative rearrangement of chiral tetrahydro-β-carboline precursors into the corresponding oxindoles was investigated in some detail and found to depend critically on the substitution pattern of the aliphatic amino group. These findings were exploited for the preparation of (-)-1, as well as of the unnatural optical antipode (+)-1, starting from 5-hydroxy-L-tryptophan as the single source from the chiral pool.

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氧吲哚生物碱(−)-马丝氨酸的合成

合成(-)-马filine((-)-1)，一种最近从马蹄铁中分离的代谢物。对手性四氢β-羰基前体氧化重排成相应的氧吲哚的非对映面选择性进行了一些详细的研究，发现其主要依赖于脂肪族氨基的取代模式。这些发现被用于制备(-)-1，以及非自然光学对映体(+)-1，从5-羟基- l -色氨酸作为手性池的单一来源开始。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.

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