| Enantioefficient synthesis of alpha-ergocryptine: first direct synthesis of (+)-lysergic acid. | |
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MedLine Citation:
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PMID: 15373483 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The first direct synthesis of (+)-lysergic acid (2a) suitable for scale-up has been achieved by the following reaction sequence. Bromoketones 4d or 4g were allowed to react with amine 5 followed by deprotection, and the resulting diketone 6c was transformed into the unsaturated ketone (+/-)-7 by the LiBr/Et(3)N system. Resolution afforded (+)-7, which was further transformed by Schöllkopf's method into the mixture of esters 2e and 2f. Upon hydrolysis the latter mixture afforded (+)-2a. The peptide part of alpha-ergocryptine (1) was prepared according to the Sandoz method; the stereoefficiency, however, has been significantly improved by applying a new resolution method and recycling the undesired enantiomer. Coupling the peptide part with lysergic acid afforded 1. Having synthetic (+)-7 in hand, we can claim the total synthesis of all the alkaloids which were prepared earlier from (+)-7 that had been obtained through degradation of natural lysergic acid. |
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Authors:
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István Moldvai; Eszter Temesvári-Major; Mária Incze; Eva Szentirmay; Eszter Gács-Baitz; Csaba Szántay |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 69 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2004 Sep |
Date Detail:
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Created Date: 2004-09-17 Completed Date: 2004-11-01 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 5993-6000 Citation Subset: IM |
Affiliation:
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Chemical Research Center, Institute of Biomolecular Chemistry, Hungarian Academy of Sciences, POB 17, H-1525 Budapest, Hungary. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Catalysis Ergolines / chemical synthesis* Indoles / chemistry Lysergic Acid / chemical synthesis* Molecular Structure Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Ergolines; 0/Indoles; 511-09-1/ergocryptine; 82-58-6/Lysergic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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