Synthesis of the fungal natural product (-)-xylariamide A

نویسندگان

  • Rohan A. Davis
  • Mike Kotiw
چکیده

The first synthesis of the fungal natural product (-)-xylariamide A 1 is reported. N,Obis(trimethylsilyl)acetamide induced coupling of D-tyrosine with (E)-but-2-enedioic acid 2,5dioxo-pyrrolidin-1-yl ester methyl ester 5 produced the dechloro natural product 6, which was subsequently monochlorinated using oxone and KCl to yield synthetic 1. (-)Xylariamide A 1, (+)-xylariamide A 2 and (-)-dechloroxylariamide A 6 displayed no cytotoxic or antimicrobial activity.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Fungal cyclooligomer depsipeptides: from classical biochemistry to combinatorial biosynthesis.

This review surveys the biological activities and the iterative and recursive biosynthetic mechanisms of fungal cyclooligomer depsipeptides, and their structural diversification by various combinatorial biosynthetic methods.

متن کامل

SYNTHESIS OF (k) - 6,8-DIHYDROXY-3- ISOPROPYL-7-METHYLISOCHROMAN

The title isochroman ( 8 ) was synthesized as a suitable substrate for acetoxylation studies leading to an intermediate of type (4), expected to afford, on condensation with diketen, the fungal metabolite "rotiorin" type linear product (1). Cyclocondensation of alcohol (6), obtained by the reduction of ketone (5) with paraform in the presence of anhydrous aluminum chloride afforded the dim...

متن کامل

Antifungal Effects of Four Plant Essential Oils on Botrytis cinerea in Laboratory Conditions

Background: Essential oils are very complex mixtures of compounds with variety of biological properties Objective: In the present study, the effect of Cumin (Cuminum cyminum), Sage (Salvia officinalis), Basil (Ocimum basilicum) essential oil at 250, 500, 750 and 1000 µL.L-1 and Thyme essential oil at 30, 60, 120, 250µL.L-1 on growth of Botrytis cinerea was investigated in in vitro condition. ...

متن کامل

Investigation of CO2 and H2O Addition to Natural Gas for Production of Synthesis Gas

General modeling and optimization of syngas production via noncatalytic autothermal partial oxidation of methane are carried out using our developed scientific software which was based on the minimization of total Gibbs energy. In this work, a novel application of the direct search and Newton-Raphson methods was introduced to apply to optimization of a complex chemical reaction. Sensitivity ana...

متن کامل

Synthesis and spectroscopic characterisation of a combinatorial library based on the fungal natural product 3-chloro-4-hydroxyphenylacetamide.

Parallel solution-phase chemistry has yielded a series of secondary amide analogues of the fungal natural product 3-chloro-4-hydroxyphenylacetamide. 3-Chloro-4-hydroxyphenylacetic acid was coupled to a variety of primary amines using 1-ethyl-3-(3'-dimethylamino- propyl)-carbodiimide hydrochloride. The desired products were obtained in good yield and high purity following rapid silica purificati...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2006