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.

Key words

polycyclic polyprenylated acylphloroglucinols - cyclohexanone - Claisen rearrangement - Oppolzer’s camphorsultam - Dieckmann condensation

Publication History

Received: 30 November 2024

Accepted after revision: 27 January 2025

Accepted Manuscript online:
27 January 2025

Article published online:
14 March 2025

• References and Notes

• 1 Current address: Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan.
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