Synthesis of (-)-ilimaquinone via a radical decarboxylation and quinone addition reaction.
[reaction: see text] A stereoselective synthesis of (-)-ilimaquinone (4) is presented. The synthetic strategy is based on a novel radical decarboxylation and quinone addition methodology that produces quinone 7 from reaction of thiohydroxamic acid derivative 8 with benzoquinone (9). Final functionalization of 7 to ilimaquinone (4) is achieved by exploring the electronic effects of the residual thiopyridyl group.
Ling
Taotao
T
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
Poupon
Erwan
E
Rueden
Erik J
EJ
Theodorakis
Emmanuel A
EA
D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D011161:Porifera / Q000737:chemistry; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D011809:Quinones; D012717:Sesquiterpenes; C467077:ilimaquinone