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Chemical and Pharmaceutical Bulletin
Vol. 56 (2008) No. 3 P 250-253

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http://doi.org/10.1248/cpb.56.250

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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.

Copyright © 2008 The Pharmaceutical Society of Japan

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