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An Efficient Asymmetric Synthesis of Prostaglandin E 1
Author(s) -
Rodríguez Ana,
Nomen Miguel,
Spur Bernd Werner,
Godfroid JeanJacques
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199910)1999:10<2655::aid-ejoc2655>3.0.co;2-2
Subject(s) - chemistry , kinetic resolution , catalysis , ketone , enantioselective synthesis , furan , conjugate , yield (engineering) , silylation , cleavage (geology) , hydrolysis , total synthesis , organic chemistry , stereochemistry , medicinal chemistry , mathematical analysis , materials science , mathematics , geotechnical engineering , fracture (geology) , engineering , metallurgy
An asymmetric total synthesis of Prostaglandin E 1 ( 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 (–)‐PGE 1 5 in high yield.