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

1 Citation (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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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.",

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AU - Kato, Nobuki

AU - Miyagawa, Saki

AU - Nomoto, Haruna

AU - Nakayama, Misuzu

AU - Iwashita, Makoto

AU - Ueda, Minoru

PY - 2020/4/1

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AB - 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.

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KW - coronatine

KW - jasmonates

KW - optical resolution

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