A scalable synthesis of (+)-coronafacic acid

Nobuki Kato; Saki Miyagawa; Haruna Nomoto; Misuzu Nakayama; Makoto Iwashita; Minoru Ueda

doi:10.1002/chir.23172

A scalable synthesis of (+)-coronafacic acid

Nobuki Kato, Saki Miyagawa, Haruna Nomoto, Misuzu Nakayama, Makoto Iwashita, Minoru Ueda

SCI - Chemistry

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

3 Citations (Scopus)

Abstract

A facile, efficient, and scalable synthesis of optically pure coronafacic acid by resolution of racemic coronafacic acid obtained using an improved version of Watson's method has been developed. By optimizing the boron-mediated aldol reaction of Watson, we were able to prepare 2.1 g of racemic coronafacic acid. This was coupled with (S)-4-isopropyl-2-oxazolidinone to give a mixture of diastereomeric coronafacyl oxazolidinones, which were readily separable by silica-gel column chromatography to give 630 mg of optically pure (+)-coronafacic acid.

Original language	English
Pages (from-to)	423-430
Number of pages	8
Journal	Chirality
Volume	32
Issue number	4
DOIs	https://doi.org/10.1002/chir.23172
Publication status	Published - 2020 Apr 1

Keywords

boron-mediated aldol reaction
coronafacic acid
coronatine
jasmonates
optical resolution

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.23172

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title = "A scalable synthesis of (+)-coronafacic acid",

abstract = "A facile, efficient, and scalable synthesis of optically pure coronafacic acid by resolution of racemic coronafacic acid obtained using an improved version of Watson's method has been developed. By optimizing the boron-mediated aldol reaction of Watson, we were able to prepare 2.1 g of racemic coronafacic acid. This was coupled with (S)-4-isopropyl-2-oxazolidinone to give a mixture of diastereomeric coronafacyl oxazolidinones, which were readily separable by silica-gel column chromatography to give 630 mg of optically pure (+)-coronafacic acid.",

keywords = "boron-mediated aldol reaction, coronafacic acid, coronatine, jasmonates, optical resolution",

author = "Nobuki Kato and Saki Miyagawa and Haruna Nomoto and Misuzu Nakayama and Makoto Iwashita and Minoru Ueda",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research for MU from MEXT, Japan (nos. 26282207, 17H06407, and 17H00885), for NK (no. 19K06968), Sunbor Grant (NK), JSPS A3 Foresight Program (MU), and JSPS Core-to-Core Program Asian Chemical Biology Initiative (MU). Funding Information: This work was supported by a Grant‐in‐Aid for Scientific Research for MU from MEXT, Japan (nos. 26282207, 17H06407, and 17H00885), for NK (no. 19K06968), Sunbor Grant (NK), JSPS A3 Foresight Program (MU), and JSPS Core‐to‐Core Program Asian Chemical Biology Initiative (MU). Publisher Copyright: {\textcopyright} 2020 Wiley Periodicals, Inc.",

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AU - Kato, Nobuki

AU - Miyagawa, Saki

AU - Nomoto, Haruna

AU - Nakayama, Misuzu

AU - Iwashita, Makoto

AU - Ueda, Minoru

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research for MU from MEXT, Japan (nos. 26282207, 17H06407, and 17H00885), for NK (no. 19K06968), Sunbor Grant (NK), JSPS A3 Foresight Program (MU), and JSPS Core-to-Core Program Asian Chemical Biology Initiative (MU). Funding Information: This work was supported by a Grant‐in‐Aid for Scientific Research for MU from MEXT, Japan (nos. 26282207, 17H06407, and 17H00885), for NK (no. 19K06968), Sunbor Grant (NK), JSPS A3 Foresight Program (MU), and JSPS Core‐to‐Core Program Asian Chemical Biology Initiative (MU). Publisher Copyright: © 2020 Wiley Periodicals, Inc.

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KW - jasmonates

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A scalable synthesis of (+)-coronafacic acid

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Keywords

ASJC Scopus subject areas

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