Studies toward the total synthesis of popolohuanone E: enantioselective synthesis of 8-O-methylpopolohuanone E.
[structure: see text]. 8-O-methylpopolohuanone E (2) was synthesized in a highly convergent manner starting from the cis-fused decalin derivative accessible from the (-)-Wieland-Miescher ketone analogue. The synthetic method features a biogenetic-type annulation of the phenolic and quinone segments to regioselectively construct the central tricyclic ring system as the key step.
Katoh
T
T
Sagami Chemical Research Center, Nishi-Ohnuma, Sagamihara, Kanagawa 229-0012, Japan. takatoh@alles.or.jp
Nakatani
M
M
Shikita
S
S
Sampe
R
R
Ishiwata
A
A
Ohmori
O
O
Nakamura
M
M
Terashima
S
S
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D059005:Topoisomerase II Inhibitors
C437123:8-O-methylpopolohuanone E; D004791:Enzyme Inhibitors; D012717:Sesquiterpenes; D059005:Topoisomerase II Inhibitors