The first total synthesis of (-)-solanapyrone E based on domino Michael strategy.
[figure: see text] A phytotoxin, solanapyrone E, has been synthesized from the decalone prepared by the domino Michael reaction of the kinetic enolate of optically pure acetylcyclohexene with methyl crotonate. After several transformations on the decalone ring, condensation of a methyl acetoacetate equivalent installed a pyrone moiety and introduction of a hydroxymethyl unit into the pyrone ring furnished solanapyrone E.
Hagiwara
H
H
Graduate School of Science and Technology and Faculty of Engineering, Niigata University, 8050, 2-nocho, Ikarashi, Niigata 950-2181, Japan. hagiwara@gs.niigata-u.ac.jp
Kobayashi
K
K
Miya
S
S
Hoshi
T
T
Suzuki
T
T
Ando
M
M
D000528:Alternaria; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D009183:Mycotoxins / Q000138:chemical synthesis* / Q000737:chemistry; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009183:Mycotoxins; D009281:Naphthalenes; D011753:Pyrones; C113269:solanapyrone B