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A New Route to 6a‐Carbacyclins–Synthesis of a Stable, Biologically Potent Prostacyclin Analogue
Author(s) -
Skuballa Werner,
Vorbrüggen Helmut
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198110461
Subject(s) - prostacyclin , chemistry , stereochemistry , octane , biological activity , bicyclic molecule , lactone , vasodilation , platelet aggregation , derivative (finance) , platelet , pharmacology , biochemistry , biology , medicine , in vitro , organic chemistry , economics , financial economics
6a‐Carbacyclin (1) (X = CH 2 , R = CH(CH 3 )CH 2 CCCH 3 ), a potent vasodilator and inhibitor of blood‐platelet aggregation , exhibits the same activity‐profile and comparable efficacy as prostacyclin, but, in contrast to prostycyclin, is much more stable. It was prepared from the commercially available Corey lactone (2) (R 1 = H) via the bicyclo[3.3.0]octane derivative (3) .