An Efficient Asymmetric Synthesis of Prostaglandin E1

Autor:	Miguel Nomen, Bernd W. Spur, Ana Rodríguez, Jean-Jacques Godfroid
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Ketone Silylation Reaction step Organic Chemistry Enantioselective synthesis Total synthesis Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Enzymatic hydrolysis Physical and Theoretical Chemistry CBS catalyst
Zdroj:	European Journal of Organic Chemistry. 1999:2655-2662
ISSN:	1099-0690 1434-193X
DOI:	10.1002/(sici)1099-0690(199910)1999:10<2655::aid-ejoc2655>3.0.co;2-2
Popis:	An asymmetric total synthesis of Prostaglandin E1 (5) has been achieved in a two-component coupling process. The chiral hydroxycyclopentenone 6 was readily available from furan with 96% ee. The key reaction step was a kinetic enzymatic resolution followed by an in situ inversion. A catalytic asymmetric reduction of the γ-iodo vinyl ketone 19 with the Corey CBS catalyst gave the ω-side chain 7 with >96% ee. Conjugate addition using the reaction with dilithiocyanocuprate followed by mild cleavage of the silyl protective groups and enzymatic hydrolysis of the methyl ester 22 gave (–)-PGE15in high yield.
Databáze:	OpenAIRE
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