Enantioselective Synthesis of Four Isomers of 3-Hydroxy-4-Methyltetradecanoic Acid, the Constituent of Antifungal Cyclodepsipeptides W493 A and B

Ken-ichi NIHEI; Kimiko HASHIMOTO; Kazuo MIYAIRI; Toshikatsu OKUNO

doi:10.1271/bbb.69.231

Organic Chemistry Notes

Enantioselective Synthesis of Four Isomers of 3-Hydroxy-4-Methyltetradecanoic Acid, the Constituent of Antifungal Cyclodepsipeptides W493 A and B

Ken-ichi NIHEI, Kimiko HASHIMOTO, Kazuo MIYAIRI, Toshikatsu OKUNO

著者情報

キーワード: Sharpless epoxidation, W493 A, W493 B, cyclodepsipeptide, 3-hydroxy-4-methyltetradecanoic acid

ジャーナルフリー

2005 年 69 巻 1 号 p. 231-234

DOI https://doi.org/10.1271/bbb.69.231

詳細

抄録

Four possible stereoisomers of 3-hydroxy-4-methyltetradecanoic acid were enantioselectively synthesized by using Sharpless epoxidation and a subsequent epoxide-ring opening reaction with trimethylaluminum as the key steps. The absolute configuration of the β-oxyacid component of antifungal cyclodepsipeptides W493 A and B was consequently determined as 3S,4R.

責任著者(Corresponding author)

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