Stereoselective synthesis of scyphostatin hydrophilic moiety

Kazuaki Kuwata; Masashi Suzuki; Yoshikazu Inami; Kengo Hanaya; Takeshi Sugai; Mitsuru Shoji

doi:10.1016/j.tetlet.2014.03.077

Stereoselective synthesis of scyphostatin hydrophilic moiety

Kazuaki Kuwata, Masashi Suzuki, Yoshikazu Inami, Kengo Hanaya, Takeshi Sugai, Mitsuru Shoji

School of Pharmaceutical Sciences

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

5 Citations (Scopus)

Abstract

A stereoselective synthesis of scyphostatin hydrophilic moiety was accomplished. Substrate- and reagent-controlled dihydroxylation of tri- and monosubstituted alkenes afforded desired diols, respectively. Chemo- and stereoselective allylation of α-(methoxycarbonyl)cyclohexanone provided allylcyclohexanol. Oxidative cleavage of glycol and subsequent β-elimination of siloxycyclohexanone furnished the desired epoxycyclohexenone.

Original language	English
Pages (from-to)	2856-2858
Number of pages	3
Journal	Tetrahedron Letters
Volume	55
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2014.03.077
Publication status	Published - 2014 Apr 23

Keywords

Epoxycyclohexenone
Hydrophilic moiety
Scyphostatin
Stereoselective allylation
Stereoselective dihydroxylation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.03.077

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title = "Stereoselective synthesis of scyphostatin hydrophilic moiety",

abstract = "A stereoselective synthesis of scyphostatin hydrophilic moiety was accomplished. Substrate- and reagent-controlled dihydroxylation of tri- and monosubstituted alkenes afforded desired diols, respectively. Chemo- and stereoselective allylation of α-(methoxycarbonyl)cyclohexanone provided allylcyclohexanol. Oxidative cleavage of glycol and subsequent β-elimination of siloxycyclohexanone furnished the desired epoxycyclohexenone.",

keywords = "Epoxycyclohexenone, Hydrophilic moiety, Scyphostatin, Stereoselective allylation, Stereoselective dihydroxylation",

author = "Kazuaki Kuwata and Masashi Suzuki and Yoshikazu Inami and Kengo Hanaya and Takeshi Sugai and Mitsuru Shoji",

note = "Funding Information: This work was supported by MEXT -Supported Program for the Strategic Research Foundation at Private Universities, 2011–2015. ",

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doi = "10.1016/j.tetlet.2014.03.077",

language = "English",

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TY - JOUR

T1 - Stereoselective synthesis of scyphostatin hydrophilic moiety

AU - Kuwata, Kazuaki

AU - Suzuki, Masashi

AU - Inami, Yoshikazu

AU - Hanaya, Kengo

AU - Sugai, Takeshi

AU - Shoji, Mitsuru

N1 - Funding Information: This work was supported by MEXT -Supported Program for the Strategic Research Foundation at Private Universities, 2011–2015.

PY - 2014/4/23

Y1 - 2014/4/23

N2 - A stereoselective synthesis of scyphostatin hydrophilic moiety was accomplished. Substrate- and reagent-controlled dihydroxylation of tri- and monosubstituted alkenes afforded desired diols, respectively. Chemo- and stereoselective allylation of α-(methoxycarbonyl)cyclohexanone provided allylcyclohexanol. Oxidative cleavage of glycol and subsequent β-elimination of siloxycyclohexanone furnished the desired epoxycyclohexenone.

AB - A stereoselective synthesis of scyphostatin hydrophilic moiety was accomplished. Substrate- and reagent-controlled dihydroxylation of tri- and monosubstituted alkenes afforded desired diols, respectively. Chemo- and stereoselective allylation of α-(methoxycarbonyl)cyclohexanone provided allylcyclohexanol. Oxidative cleavage of glycol and subsequent β-elimination of siloxycyclohexanone furnished the desired epoxycyclohexenone.

KW - Epoxycyclohexenone

KW - Hydrophilic moiety

KW - Scyphostatin

KW - Stereoselective allylation

KW - Stereoselective dihydroxylation

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DO - 10.1016/j.tetlet.2014.03.077

M3 - Article

AN - SCOPUS:84899048894

SN - 0040-4039

VL - 55

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EP - 2858

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Stereoselective synthesis of scyphostatin hydrophilic moiety

Abstract

Keywords

ASJC Scopus subject areas

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