An efficient chemoenzymatic route to the antidepressants (R)-fluoxetine and (R)-tomoxetine

✍ Scribed by Franz Bracher; Thomas Litz

• Book ID: 103992299
• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 413 KB
• Volume: 4
• Category: Article
• ISSN: 0968-0896
• DOI: 10.1016/0968-0896(96)00077-6

✦ Synopsis

Abstraet--(S)-l-Phenyl-3-buten-l-ol (1), prepared in high optical purity by enzymatic resolution of the racemate, is a convenient building block for the synthesis of (R)-fluoxetine (7a) and (R)-tomoxetine (7b). Compound 1 was converted to the title drugs by ctherification with appropriate phenols under Mitsunobu conditions, ozonolysis of the terminal double bond, mesylation of the resulting alcohol and substitution with methylamine.