A Convergent Approach to Dibenzodioxocinones: Synthesis of Racemic Penicillide

Deng, Chun‐Lin; Zhang, Qiao; Fang, Lisong; Lei, Xinsheng; Lin, Guo‐Qiang

doi:10.1002/hlca.201100405

Cited by 4 publications

(1 citation statement)

References 16 publications

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“…Given the fact that the analog bakuchiol shows various biological activities, we have put ∆ 3 -2-hydroxybakuchiol into our natural product-based drug discovery program [27,28,29,30]. Recently, a facile asymmetric synthesis of ∆ 3 -2-hydroxybakuchiol was established and the compound was tested for antiosteoporosis effects [31,32].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ∆3-2-Hydroxybakuchiol Analogues and Their Growth Inhibitory Activity against Rat UMR106 Cells

Zhao

Shan

et al. 2014

Molecules

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A series of ∆ 3 -2-hydroxybakuchiol analogues have been synthesized and tested for their growth inhibitory activity against rat UMR106 cells by using the MTT method. Some of them exhibit enhanced activities compared with the natural product, and the preliminary SAR profile shows that the chain tail on the natural product could be subtly modified to enhance the activity and the aromatic moiety or the terminal olefin on the main chain can also be modified without any evident loss of activity. The stereo-configuration of the quaternary chiral center has an important influence on the activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis of ∆3-2-Hydroxybakuchiol Analogues and Their Growth Inhibitory Activity against Rat UMR106 Cells

Zhao

Shan

et al. 2014

Molecules

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Synthesis and Evaluation of the Analogues of Penicillide against Cholesterol Ester Transfer Protein

et al. 2013

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Biomimetic Synthesis of Functionalized γ‐Resorcylates from Dioxinone Derivatives

Blencowe

Barrett

2014

Eur J Org Chem

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Biomimetic syntheses of functionalized γ‐resorcylates from 2,2,6‐trimethyl‐4H‐1,3‐dioxin‐4‐one derivatives are reported. Cross metathesis of 2,2‐dimethyl‐6‐vinyl‐4H‐1,3‐dioxin‐4‐one with homoallylic esters or aldol reactions of tert‐butyl or benzyl esters with 1‐(2,2‐dimethyl‐4‐oxo‐4H‐1,3‐dioxin‐6‐yl)‐acetone and related ketones followed by aromatization under mild Appel‐type reaction conditions gave a range of γ‐resorcylates.

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A Convergent Approach to Dibenzodioxocinones: Synthesis of Racemic Penicillide

Abstract: A convergent approach to dibenzodioxocinones was explored, thereby racemic penicillide ((±)‐1a) could be obtained in 13 steps in 4.2% overall yield, based on 5‐amino‐2‐methylphenol (5) (Schemes 2–4).

Cited by 4 publications

References 16 publications

Synthesis of ∆3-2-Hydroxybakuchiol Analogues and Their Growth Inhibitory Activity against Rat UMR106 Cells

Synthesis of ∆3-2-Hydroxybakuchiol Analogues and Their Growth Inhibitory Activity against Rat UMR106 Cells

Synthesis and Evaluation of the Analogues of Penicillide against Cholesterol Ester Transfer Protein

Biomimetic Synthesis of Functionalized γ‐Resorcylates from Dioxinone Derivatives

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