Chemoenzymatic synthesis of the C10-C23 segment of dictyostatin.
[reaction: see text] Employing 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.
Prusov
Evgeny
E
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany.
Röhm
Hartmut
H
Maier
Martin E
ME
D000447:Aldehydes / Q000138:chemical synthesis*; D002384:Catalysis; D008049:Lipase / Q000378:metabolism*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D018942:Macrolides; C470814:dictyostatin; D008049:Lipase