Enantiocontrolled synthesis of jasmonates via tandem retro-Diels-Alder-ene reaction activated by a silyl substituent.
[reaction: see text] An enantiocontrolled synthesis of (-)-methyl 6-epi-cucurbate and (+)-methyl jasmonate was established from a chiral tricyclic lactone via a new type of tandem retro-Diels-Alder-ene reaction activated by a trimethysilyl substituent as the key step.
Suzuki
Katsufumi
K
Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
Inomata
Kohei
K
Endo
Yasuyuki
Y
D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D054883:Oxylipins; D010937:Plant Growth Regulators / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D003517:Cyclopentanes; D007769:Lactams; D054883:Oxylipins; D010937:Plant Growth Regulators; C485137:methyl 6-epi-cucurbate; C011006:jasmonic acid