Synthesis of (−)-okundoperoxide and determination of the absolute configuration of natural (+)-okundoperoxide

Naoki Mori; Daichi Sakoda; Hidenori Watanabe

doi:10.1016/j.tetlet.2017.08.064

Synthesis of (−)-okundoperoxide and determination of the absolute configuration of natural (+)-okundoperoxide

Naoki Mori, Daichi Sakoda, Hidenori Watanabe

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

2 Citations (Scopus)

Abstract

The first enantioselective synthesis of (3S,4aR,8aR)-1 (the enantiomer of natural okundoperoxide) has been accomplished. The synthesis features: 1) stereoselective installation of the peroxy functionality (16 → 17); 2) ring opening of peroxyacetal and subsequent intramolecular reaction between the hydroperoxide and the vinyl epoxide to form the peroxy six-membered ring (5 → 1). The absolute configuration of okundoperoxide was determined to be 3R,4aS,8aS by comparing specific rotations of the synthetic sample and the natural product.

Original language	English
Pages (from-to)	3884-3886
Number of pages	3
Journal	Tetrahedron Letters
Volume	58
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2017.08.064
Publication status	Published - 2017
Externally published	Yes

Keywords

Antibacterial
Antimalarial
Determination of the absolute configuration
Endoperoxide
Okundoperoxide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2017.08.064

Cite this

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title = "Synthesis of (−)-okundoperoxide and determination of the absolute configuration of natural (+)-okundoperoxide",

abstract = "The first enantioselective synthesis of (3S,4aR,8aR)-1 (the enantiomer of natural okundoperoxide) has been accomplished. The synthesis features: 1) stereoselective installation of the peroxy functionality (16 → 17); 2) ring opening of peroxyacetal and subsequent intramolecular reaction between the hydroperoxide and the vinyl epoxide to form the peroxy six-membered ring (5 → 1). The absolute configuration of okundoperoxide was determined to be 3R,4aS,8aS by comparing specific rotations of the synthetic sample and the natural product.",

keywords = "Antibacterial, Antimalarial, Determination of the absolute configuration, Endoperoxide, Okundoperoxide",

author = "Naoki Mori and Daichi Sakoda and Hidenori Watanabe",

note = "Funding Information: This work was supported by Grant-in-Aid for Young Scientists (B) (No. 24780110 ) to N.M. from JSPS . Publisher Copyright: {\textcopyright} 2017 Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.tetlet.2017.08.064",

language = "English",

volume = "58",

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journal = "Tetrahedron Letters",

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publisher = "Elsevier Limited",

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T1 - Synthesis of (−)-okundoperoxide and determination of the absolute configuration of natural (+)-okundoperoxide

AU - Mori, Naoki

AU - Sakoda, Daichi

AU - Watanabe, Hidenori

N1 - Funding Information: This work was supported by Grant-in-Aid for Young Scientists (B) (No. 24780110 ) to N.M. from JSPS . Publisher Copyright: © 2017 Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2017

Y1 - 2017

N2 - The first enantioselective synthesis of (3S,4aR,8aR)-1 (the enantiomer of natural okundoperoxide) has been accomplished. The synthesis features: 1) stereoselective installation of the peroxy functionality (16 → 17); 2) ring opening of peroxyacetal and subsequent intramolecular reaction between the hydroperoxide and the vinyl epoxide to form the peroxy six-membered ring (5 → 1). The absolute configuration of okundoperoxide was determined to be 3R,4aS,8aS by comparing specific rotations of the synthetic sample and the natural product.

AB - The first enantioselective synthesis of (3S,4aR,8aR)-1 (the enantiomer of natural okundoperoxide) has been accomplished. The synthesis features: 1) stereoselective installation of the peroxy functionality (16 → 17); 2) ring opening of peroxyacetal and subsequent intramolecular reaction between the hydroperoxide and the vinyl epoxide to form the peroxy six-membered ring (5 → 1). The absolute configuration of okundoperoxide was determined to be 3R,4aS,8aS by comparing specific rotations of the synthetic sample and the natural product.

KW - Antibacterial

KW - Antimalarial

KW - Determination of the absolute configuration

KW - Endoperoxide

KW - Okundoperoxide

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

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Synthesis of (−)-okundoperoxide and determination of the absolute configuration of natural (+)-okundoperoxide

Abstract

Keywords

ASJC Scopus subject areas

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