Synthetic Studies of Polycyclic Polyprenylated Acylphloroglucinols: Asymmetric Construction of a Cyclohexanone Moiety

Abstract As a common intermediate for polycyclic polyprenylated acylphloroglucinols (PPAPs), we successfully synthesized a cyclohexanone moiety that contains two adjacent stereocenters, one of which is a quaternary carbon. Our synthetic strategy relied on an asymmetric Claisen rearrangement using Oppolzer’s camphorsultam and a regioselective Dieckmann condensation.

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Publication Details

Journal
Synlett
Published
2025-01-27
DOI
https://doi.org/10.1055/a-2526-0619
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthetic Studies of Polycyclic Polyprenylated Acylphloroglucinols: Asymmetric Construction of a Cyclohexanone Moiety

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Synthetic Studies of Polycyclic Polyprenylated Acylphloroglucinols: Asymmetric Construction of a Cyclohexanone Moiety

Ken‐ichi Takao, Kohei Abo, Genichiro Okuyama, Daisuke Aoki, Takashi Akiya, Akihiro Ogura, Keisuke Yoshida, Satoshi Nanataki, Hayato Onozawa
article en

Abstract

Abstract As a common intermediate for polycyclic polyprenylated acylphloroglucinols (PPAPs), we successfully synthesized a cyclohexanone moiety that contains two adjacent stereocenters, one of which is a quaternary carbon. Our synthetic strategy relied on an asymmetric Claisen rearrangement using Oppolzer’s camphorsultam and a regioselective Dieckmann condensation.

SynlettVol. 36(10)
Keio University (JP), Meijo University (JP)
Japan Society for the Promotion of Science
Openalex Percentile: Top 99%
Carbohydrate Chemistry and Synthesis
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