Document Detail


Enantioefficient synthesis of alpha-ergocryptine: first direct synthesis of (+)-lysergic acid.
MedLine Citation:
PMID:  15373483     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
István Moldvai; Eszter Temesvári-Major; Mária Incze; Eva Szentirmay; Eszter Gács-Baitz; Csaba Szántay
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Sep 
Date Detail:
Created Date:  2004-09-17     Completed Date:  2004-11-01     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5993-6000     Citation Subset:  IM    
Affiliation:
Chemical Research Center, Institute of Biomolecular Chemistry, Hungarian Academy of Sciences, POB 17, H-1525 Budapest, Hungary.
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Ergolines / chemical synthesis*
Indoles / chemistry
Lysergic Acid / chemical synthesis*
Molecular Structure
Stereoisomerism
Chemical
Reg. No./Substance:
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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