Two Novel Skeletal Rearrangements Involving in the C Ring of C19-Diterpenoid Alkaloid Deltaline Derivatives

Chun-Lan Zou; Xiao-Yu Liu; Feng-Peng Wang; Qiao-Hong Chen

doi:10.1248/cpb.56.250

Regular Articles

Two Novel Skeletal Rearrangements Involving in the C Ring of C₁₉-Diterpenoid Alkaloid Deltaline Derivatives

Chun-Lan Zou, Xiao-Yu Liu, Feng-Peng Wang, Qiao-Hong Chen

Author information

Keywords: C₁₉-diterpenoid alkaloid, deltaline, Wagner–Meerwein rearrangement, Grob fragmentation, 9,10-seco C₁₉-diterpenoid alkaloid

JOURNAL FREE ACCESS

2008 Volume 56 Issue 3 Pages 250-253

DOI https://doi.org/10.1248/cpb.56.250

Details

Abstract

Treatment of compounds 2 and 5, both from the C₁₉-diterpenoid alkaloid deltaline 1, with 5% NaOH methanol (room temperature, 16 h) and NaOH-N,N-dimethylformamide (reflux, 10 h) led to the two novel skeletal rearrangement products 4 (90%) and 6 (62%), respectively, involving Wagner–Meerwein rearrangement and Grob fragmentation. Their structures were fully characteristized based on 2D NMR and HR-MS data.

Corresponding author

Register with J-STAGE for free!