Total synthesis of (±)-picropodophyllone
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 271-276
- https://doi.org/10.1039/p19820000271
Abstract
Following model studies, the synthesis of (±)-picropodophyllone was completed by first cyclopropanating the appropriate chalcone (11) with ethoxycarbonyl dimethylsulphonium methylide. Treatment of the resulting cyclopropyl ketone with stannic chloride in either benzene or methylene chloride failed but in nitromethane the tetralone (1Oa) was formed. The lactose ring was completed using formaldehyde with an overall yield based on chalcone of 40%.Keywords
This publication has 3 references indexed in Scilit:
- Synthetic studies on lignan lactones: aryl dithiane route to (.+-.)-podorhizol and (.+-.)-isopodophyllotoxone and approaches to the stegane skeletonThe Journal of Organic Chemistry, 1978
- Synthesis of (±)-podorhizone via intermediate α-hydroxyalkylation of a β-benzyl γ-butyrolactoneJournal of the Chemical Society, Chemical Communications, 1978
- Tumor Inhibitors VII. Podophyllotoxin, the Active Principle of Juniperus virginianaJournal of Pharmaceutical Sciences, 1965