Synthetic and biological studies on the spiro-mamakone system.
An exploration of the chemistry of the spiro-mamakone system, exemplified by the cytotoxic, fungal metabolite spiro-mamakone A, is presented. The first reported synthesis of the spiro-mamakone carbon skeleton was achieved, as well as the synthesis of a variety of closely related analogues of the natural product. Biological testing of the synthetic analogues generated a structure-activity profile for the natural product, establishing the importance of the enedione moiety to biological activity.
Murphy
Annabel C
AC
Department of Chemistry, University of Canterbury, Christchurch, New Zealand.
Devenish
Sean R A
SR
Muscroft-Taylor
Andrew C
AC
Blunt
John W
JW
Munro
Murray H G
MH
D000080:Acetals; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001688:Biological Products / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D051379:Mice; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000080:Acetals; D000970:Antineoplastic Agents; D001688:Biological Products; D009281:Naphthalenes; D013141:Spiro Compounds; C517106:spiro-mamakone A