A Convenient Method for Retro-Cycloadditon of Adducts from Steroidal 5, 7-Dienes and 4-Phenyl-1, 2, 4-triazolidine-3, 5-dione and Application to the Syntheses of Biosynthetic Intermediates of Ergosterol

Yoji TACHIBANA

doi:10.1248/cpb.46.1454

Yoji TACHIBANA

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Keywords: retro-cycloaddition, protection-deprotection, steroidal 5, 7-diene, 4-phenyl-1, 2, 4-triazolidine-3, 5-dione, 1, 8-diazabicyclo[5.4.0]undec-7-ene

JOURNAL FREE ACCESS

1998 Volume 46 Issue 9 Pages 1454-1458

DOI https://doi.org/10.1248/cpb.46.1454

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Abstract

Use of 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU) in boiling xylene was found to be a convenient method for the retro-cycloaddition of adducts of 4-phenyl-1, 2, 4-triazolidine-3, 5-dione (PTAD) with steroidal 5, 7-dienes. This process was applied to the syntheses of ergosta-5, 7, 24(28)-trien-3β-ol and ergosta-5, 7, 22, 24(28)-tetraen-3β-ol.

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