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...

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Bibliographic Details
Published in:Organic letters 2001-08, Vol.3 (17), p.2701-2704
Main Authors: Katoh, T, Nakatani, M, Shikita, S, Sampe, R, Ishiwata, A, Ohmori, O, Nakamura, M, Terashima, S
Format: Article
Language:English
Subjects:
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Magnetic Resonance Spectroscopy
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
Topoisomerase II Inhibitors
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Summary:[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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016285h