Synthesis of Novel Difluoroprostacyclin Derivatives: Unprecedented Stabilizing Effect of Fluorine Substituents | Zendy

Nakano Takashi | Zendy; Makino Mayumi | Zendy; Morizawa Yoshitomi | Zendy; Matsumura Yasushi | Zendy

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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.

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