Chemoenzymatic Synthesis of the C10−C23 Segment of Dictyostatin
2006; American Chemical Society; Volume: 8; Issue: 6 Linguagem: Inglês
10.1021/ol052917e
ISSN1523-7060
AutoresEvgeny V. Prusov, H.F. Röhm, Martin E. Maier,
Tópico(s)Microbial Natural Products and Biosynthesis
ResumoEmploying enzymatic desymmetrization and resolution, respectively, the two aldehydes 8 and 20 were prepared. The precursor to aldehyde 8, meso-2,4-dimethylglutaric anhydride 3, could be obtained by base treatment of the diastereomeric mixture. Aldehyde 8 was extended to alkyne 10 by a Marshall reaction introducing four carbon atoms. Lithiation of the derived iodide 15 and trapping of the anion with amide 22 gave ketone 23. This compound led to the C10−C23 fragment 27 of dictyostatin.
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