Naturally occurring dibenzofurans. Part 2. The synthesis of schizopeltic acid
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2373-2377
- https://doi.org/10.1039/p19820002373
Abstract
The structure of schizopeltic acid as 1,7-dimethoxy-6-methoxycarbonyl 3,9-dimethyldibenzofuran-4-carboxylic acid (1) has been confirmed by rational synthesis. 6-Methoxy-4-methylbenzofuran-2-carbaldehyde (10), available from 3,5-dimethoxytoluene (4) in six steps, was converted into methyl 1-acetoxy-7-methoxy-9-methyldibenzofuran-3-carboxylate (12) by Wittig reaction with 2-carboxy-1-methoxycarbonylethyltriphenylphosphorane and subsequent ring-closure of the resultant (E)-3-methoxycarbonyl-4-(6-methoxy-4-methylbenzofuran-2-yl)but-3-enoic acid (11) with acetic anhydride. Reduction of compound (12) gave 7-methoxy-3,9-dimethyldibenzofuran-1-ol (14) which was converted into schizopeltic acid (1) by sequential formylations and oxidations.This publication has 3 references indexed in Scilit:
- Naturally occurring dibenzofurans. Part 1. A synthesis of cannabifuranJournal of the Chemical Society, Perkin Transactions 1, 1982
- Depsidone synthesis. Part 13. The total synthesis of variolaric acidJournal of the Chemical Society, Perkin Transactions 1, 1979
- Über die Inhaltsstoffe einiger Roccellaceen und die Struktur der Schizopeltsäure, eines neuen Dibenzofuran-Derivates aus Roccellina luteola FOLLM.Zeitschrift für Naturforschung B, 1967