Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain

Koichi Mikami; Teck Peng Loh; Takeshi Nakai

doi:10.1016/S0040-4039(00)82332-1

Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain

Koichi Mikami^*, Teck Peng Loh, Takeshi Nakai

^*Corresponding author for this work

Tokyo Institute of Technology

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

49 Citations (Scopus)

Abstract

Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain.

Original language	English
Pages (from-to)	6305-6308
Number of pages	4
Journal	Tetrahedron Letters
Volume	29
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4039(00)82332-1
Publication status	Published - 1988
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain",

abstract = "Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain.",

author = "Koichi Mikami and Loh, \{Teck Peng\} and Takeshi Nakai",

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AU - Mikami, Koichi

AU - Loh, Teck Peng

AU - Nakai, Takeshi

PY - 1988

Y1 - 1988

N2 - Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain.

AB - Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain.

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DO - 10.1016/S0040-4039(00)82332-1

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Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain

Abstract

ASJC Scopus Subject Areas

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