Synthesis of the C20-C34 segment of the immunosuppressant FK-506 via stereocontrolled aldol coupling application of a remote chelation effect

James D. White; Steven G. Toske; Takayuki Yakura

doi:10.1055/s-1994-22937

Synthesis of the C20-C34 segment of the immunosuppressant FK-506 via stereocontrolled aldol coupling application of a remote chelation effect

James D. White^*, Steven G. Toske, Takayuki Yakura

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

13 被引用数 (Scopus)

抄録

Stereoselective aldol condensation of an α-chiral methyl ketone, prepared from ethyl (R)-3-hydroxybutyrate, with an α-chiral aldehyde, prepared from (-)-quinic acid, was used to construct the C20-C34 segment of the immunosuppressant FK-506. Stereoselection in this process is attributed to tight coordination of the lithium enolate with a β-trityl ether thereby imparting a large steric bias to the ketone enolate.

本文言語	英語
ページ（範囲）	591-593
ページ数	3
ジャーナル	Synlett
巻	1994
号	8
DOI	https://doi.org/10.1055/s-1994-22937
出版ステータス	出版済み - 1994/08/01

ASJC Scopus 主題領域

有機化学

文献へのアクセス

10.1055/s-1994-22937

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引用スタイル

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AB - Stereoselective aldol condensation of an α-chiral methyl ketone, prepared from ethyl (R)-3-hydroxybutyrate, with an α-chiral aldehyde, prepared from (-)-quinic acid, was used to construct the C20-C34 segment of the immunosuppressant FK-506. Stereoselection in this process is attributed to tight coordination of the lithium enolate with a β-trityl ether thereby imparting a large steric bias to the ketone enolate.

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