Acid-Induced Rearrangement of Triterpenoid Hydrocarbons Belonging to the Hopane and Migrated Hopane Series

HIROYUKI AGETA; KENJI SHIOJIMA; YÔKO ARAI

doi:10.1248/cpb.35.2705

HIROYUKI AGETA, KENJI SHIOJIMA, YÔKO ARAI

Author information

Keywords: acid-induced rearrangement, triterpenoid hydrocarbon, hopane, migrated hopane, 9β-fern-7-ene, 8β-fern-9 (11) -ene, adian-5 (10) -ene, sulfuric acid, boron trifluoride

JOURNAL FREE ACCESS

1987 Volume 35 Issue 7 Pages 2705-2716

DOI https://doi.org/10.1248/cpb.35.2705

Details

Abstract

The acid-catalyzed rearrangement of triterpenoid monoenes belonging to the hopane and migrated hopane series with sulfuric acid and boron trifluoride etherate was investigated. By selecting the reaction conditions, a variety of the monoenes of these series, including three new compounds, 9βH-fern-7-ene (3c), 8βH-fern-9 (11) -ene (4b), and adian-5 (10) -ene (5b), were obtained. For comparison, oleanenes and migrated oleanenes were also subjected to the same reaction.

Corresponding author

Register with J-STAGE for free!