Synthesis of a natural product-inspired eight-membered ring lactam library via ring-closing metathesis.
We have prepared a novel speculative eight-membered lactam demonstration library based on the skeletal structure of the potent antitumor marine natural product octalactin A. The basic scaffold was readily constructed in a convergent fashion via ring-closing metathesis chemistry from the corresponding diene amides. A cursory examination of the biological properties of the library validates the relevance and significance of these structures.
Brown
Neil
N
Department of Chemistry, University of Missouri-Kansas City, 205 Spencer Chemical Laboratories, 5100 Rockhill Road, Kansas City, MO 64110, USA.
Xie
Baohan
B
Markina
Nataliya
N
Vandervelde
David
D
Perchellet
Jean-Pierre H
JP
Perchellet
Elisabeth M
EM
Crow
Kyle R
KR
Buszek
Keith R
KR
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry*; D049109:Cell Proliferation / Q000187:drug effects; D018922:HL-60 Cells; D006801:Humans; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D054852:Small Molecule Libraries / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D001688:Biological Products; D007769:Lactams; D007783:Lactones; D054852:Small Molecule Libraries; C509476:octalactin A