Total synthesis and biological evaluation of (-)-pectinatone employing a methyl-branched wax ester as key building block.
Unnatural (-)-pectinatone ((-)-3) was prepared in five steps starting from the highly methyl-branched wax ester 4, employing bromination of the ester enolate and subsequent base-induced elimination to the enoate 6 as the key step. Both (-)-3 and the amides 8b and 8c, which were isolated as by-products in the reaction sequence, displayed antimicrobial activity and cytotoxicity.
Galeyeva
Yana
Y
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart.
Helbig
Sarah
S
Morr
Michael
M
Sasse
Florenz
F
Nimtz
Manfred
M
Laschat
Sabine
S
Baro
Angelika
A
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001688:Biological Products / Q000494:pharmacology; D002460:Cell Line; D004926:Escherichia coli / Q000187:drug effects; D004952:Esters / Q000737:chemistry*; D051379:Mice; D016982:Micrococcus luteus / Q000187:drug effects; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D014885:Waxes / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D001688:Biological Products; D004952:Esters; D011753:Pyrones; D014885:Waxes; C518672:pectinatone