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Synthesis of Novel Difluoroprostacyclin Derivatives: Unprecedented Stabilizing Effect of Fluorine Substituents
Author(s) -
Nakano Takashi,
Makino Mayumi,
Morizawa Yoshitomi,
Matsumura Yasushi
Publication year - 1996
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.199610191
Subject(s) - chemistry , prostacyclin , natural product , wittig reaction , lactone , derivative (finance) , platelet aggregation , fluorine , side chain , stereochemistry , combinatorial chemistry , platelet , organic chemistry , biochemistry , financial economics , immunology , economics , biology , polymer
Markedly more stable than the natural product , di‐fluoroprostacyclin 1 inhibits ADP‐induced human platelet aggregation better than any other known prostacyclin derivative. Key steps in the synthesis of 1 are fluorination of the Corey lactone with (Ph‐SO 2 ) 2 NF in the presence of MgBr 2 and subsequent Wittig reaction to attach the α side chain.