Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue

Shijun Wen; Krystle L. Carey; Yoichi Nakao; Nobuhiro Fusetani; Graham Packham; A. Ganesan

doi:10.1021/ol070046y

Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue

Shijun Wen, Krystle L. Carey, Yoichi Nakao, Nobuhiro Fusetani, Graham Packham, A. Ganesan

Research output: Contribution to journal › Article › peer-review

55 Citations (Scopus)

Abstract

The unprecedented diastereoselective Mannich reaction of a Z-allylsulfoximine was a key step in the total synthesis of the marine natural products azumamide A and E, and an unnatural analogue. Their relative potency as histone deacetylase inhibitors was evaluated and found to correlate with predicted zinc-binding affinity.

Original language	English
Pages (from-to)	1105-1108
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	6
DOIs	https://doi.org/10.1021/ol070046y
Publication status	Published - 1 Mar 2007

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10.1021/ol070046y

Cite this

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abstract = "The unprecedented diastereoselective Mannich reaction of a Z-allylsulfoximine was a key step in the total synthesis of the marine natural products azumamide A and E, and an unnatural analogue. Their relative potency as histone deacetylase inhibitors was evaluated and found to correlate with predicted zinc-binding affinity.",

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AU - Fusetani, Nobuhiro

AU - Packham, Graham

AU - Ganesan, A.

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AB - The unprecedented diastereoselective Mannich reaction of a Z-allylsulfoximine was a key step in the total synthesis of the marine natural products azumamide A and E, and an unnatural analogue. Their relative potency as histone deacetylase inhibitors was evaluated and found to correlate with predicted zinc-binding affinity.

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