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SYNTHETIC AND MECHANISTIC STUDIES OF ERGOT ALKALOIDS

SYNTHETIC AND MECHANISTIC STUDIES OF ERGOT ALKALOIDS
麦角生物碱的合成及机理研究
批准号：
3282300
负责人：
JULIUS REBEK
金额：
$6.93万
依托单位：
UNIVERSITY OF PITTSBURGH AT PITTSBURGH
依托单位国家：
美国
项目类别：
财政年份：
1983
资助国家：
美国
项目状态：
已结题
起止时间：
1983-12-01 至 1986-11-30
来源：
https://reporter.nih.gov/project-details/3282300
关键词：
chemical reaction chemical substitution chemical synthesis nuclear magnetic resonance spectroscopy racemization tryptophan

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英文摘要
This proposal explores the use of tryptophan as a starting material for the total synthesis of ergot alkaloids. The methods involve intramolecular Friedel-Crafts reaction of a suitably protected tryptophan to give an optically active tricyclic skeleton ideally functionalized for elaboration to natural products. Either enantiomer is available from L-tryptophan. Specific targets include the ergolines lysergene and lysergol, the chanoclavines and clavicipitic acid. The latter involves a study of intramolecular amido-alkylation of the 4-position of tryptophan from which substances of biosynthetic interest should become available. Finally, a mechanistic study of the peculiar racemization and isomerization behavior of the rugulovasine ergot alkaloids is proposed.
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