A short versatile synthesis of aryltetralin lignans including deoxyisopodophyllotoxin and epi-isopodophyllotoxin
- 31 December 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1615-1623
- https://doi.org/10.1039/p19880001615
Abstract
Cyclisation of tandem conjugate addition products (10), (15), and (20), prepared by reaction of anions derived from benzyl phenyl and benzyl t-butyl sulphides with but-2-en-4-olide, affords a series of aryltetralin lignans belonging to either the ‘normal’ or the ‘retro’ lactone series. Desulphurisation of compound (15) followed by cyclisation, or desulphurisation of the cyclised product (22b), affords deoxyisopodophyllotoxin (5), while treatment of compound (22b) with mercury(II) trifluoroacetate yields epi-isopodophyllotoxin (6).This publication has 6 references indexed in Scilit:
- Synthesis of lignans related to the podophyllotoxin seriesJournal of the Chemical Society, Perkin Transactions 1, 1987
- Synthesis of lignan lactones by conjugate addition of thioacetal carbanions to butenolideJournal of the Chemical Society, Perkin Transactions 1, 1983
- Structure and synthesis of the aryltetralin lignans hypophyllanthin and nirtetralinJournal of the Chemical Society, Perkin Transactions 1, 1982
- Total synthesis of (±)-picropodophylloneJournal of the Chemical Society, Perkin Transactions 1, 1982
- Synthetic studies on lignan lactones: aryl dithiane route to (.+-.)-podorhizol and (.+-.)-isopodophyllotoxone and approaches to the stegane skeletonThe Journal of Organic Chemistry, 1978
- TYPES OF ANTICANCER AGENTS ISOLATED FROM PLANTS1976