Enantioselective total synthesis of dysidavarone A, a novel sesquiterpenoid quinone from the marine sponge Dysidea avara.
Dysidavarone A, a structurally unprecedented sesquiterpenoid quinone, was synthesized in 30 % overall yield in a longest liner sequence of 13 steps from commercially available o-vanillin. A highly strained and bridged eight-membered carbocyclic core was established by the C7-C21 carbon bond formation through a copper enolate mediated Michael addition to the internal quinone ring.
Laboratory of Synthetic and Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, 981-8558 (Japan), Fax: (+81) 22-727-0135.
Yurie
Y
Fukui
Koichi
K
Narita
Tadashi
T
Katoh
D000818:Animals; D001547:Benzaldehydes / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D047088:Dysidea; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
D001547:Benzaldehydes; D011809:Quinones; D012717:Sesquiterpenes; C581823:dysidavarone A; C060843:2-vanillin; D003300:Copper
Michael addition; copper enolate; dysidavarone A; sesquiterpenoids; total synthesis