Total Synthesis of Leukotrienes from Butadiene

Autor:	Jean-Jacques Godfroid, Bernd W. Spur, Tak H. Lee, Miguel Nomen, Ana Rodríguez
Rok vydání:	2000
Předmět:	Telomerization (dimerization) Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis chemistry.chemical_element Total synthesis lipids (amino acids peptides and proteins) Epimer respiratory system Physical and Theoretical Chemistry Catalysis Palladium
Zdroj:	European Journal of Organic Chemistry. 2000:2991-3000
ISSN:	1099-0690 1434-193X
DOI:	10.1002/1099-0690(200009)2000:17<2991::aid-ejoc2991>3.0.co;2-h
Popis:	The total synthesis of leukotrienes has been achieved starting from butadiene by a palladium-catalyzed telomerization at room temperature. A Sharpless catalytic asymmetric epoxidation generated the asymmetric centers with >94% ee. Simple transformations of the key intermediate 15 produced the leukotrienes LTA4 methyl ester (4), LTC4 (1), LTD4 (2) and LTE4 (3), as well as (14S,15S)-LTA4 methyl ester (24) and the novel [2H2]-LTA4 methyl ester (28). The use of the opposite chiral director in the Sharpless catalytic asymmetric epoxidation gave the key intermediate 15a that has been used in the synthesis of the double epimers of the leukotrienes as well as LTB4.
Databáze:	OpenAIRE
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