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

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

13 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	591-593
Number of pages	3
Journal	Synlett
Volume	1994
Issue number	8
DOIs	https://doi.org/10.1055/s-1994-22937
State	Published - 1994/08/01

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Organic Chemistry

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

abstract = "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.",

author = "White, {James D.} and Toske, {Steven G.} and Takayuki Yakura",

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AU - White, James D.

AU - Toske, Steven G.

AU - Yakura, Takayuki

PY - 1994/8/1

Y1 - 1994/8/1

N2 - 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.

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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U2 - 10.1055/s-1994-22937

DO - 10.1055/s-1994-22937

M3 - 学術論文

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ER -

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

Abstract

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