Reaction of Steroid-17α-hydroxy-17-carboxylic Acids with Carbodiimides. Synthesis of Steroid-17-spiro-5'-[2'-imino-4'-oxazolidinones] and 17-Spiro-5'-[2', 4'-oxazolidinediones]

Shunsaku NOGUCHI; Ayumi FUJII; Koki HASHITANI; Takashi ISHIZU

doi:10.1248/cpb.42.1567

Shunsaku NOGUCHI, Ayumi FUJII, Koki HASHITANI, Takashi ISHIZU

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Keywords: steroid-17-spiro compound, steroid-17α-hydroxy-17-carboxylic acid, carbodiimide, 2-imino-4-oxazolidinone, 2, 4-oxazolidinedione, anti-angiogenic activity

JOURNAL FREE ACCESS

1994 Volume 42 Issue 8 Pages 1567-1570

DOI https://doi.org/10.1248/cpb.42.1567

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Abstract

Steroid-17α-hydroxy-17-carboxylic acids (2) were allowed to react with carbodiimides (DCCI, DPCI, DTCI, EDCI) to afford 17-spiro-5'-[2'-imino-4'-oxazolidinones] (3-5, 11), 17-spiro-5'-[2', 4'-oxazolidinediones] (7-9)and N-acylureas (10), depending on the reaction conditions. The reaction in acetonitrile in the presence of CuCl₂ gave 3-5, while that in N, N-dimethylformamide gave 7-9. The reaction with DTCI under basic conditions afforded 10 along with 9.

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