Depsidone synthesis. Part 15. New metabolites of the lichen Buellia canescens(Dicks.) De Not: novel phthalide catabolites of depsidones
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 849-854
- https://doi.org/10.1039/p19810000849
Abstract
The isolation, from the lichen Buellia canescens(Dicks.) De Not., and structural determination of the new depsidones 2,7,9-trichloro-3-hydroxy-8-methoxy-1,6-dimethyldibenzo[b,e][1,4]dioxepin-11-one (dechlorodiploicin)(1) and its methyl ether dechloro-O-methyldiploicin (9), together with the novel phthalides 4-chloro-7-(3,5-dichloro-4,6-dimethoxy-2-methylphenoxy)-5-methoxyisobenzofuran-1(3H)-one (buellolide)(13) and 4,6-dichloro-7-(2,4-dichloro-3,6-dimethoxy-5-methylphenoxy)-5-methoxyisobenzofuran-1(3H)-one (canesolide)(18) are described. The synthesis of buellolide (13) is also described. It is postulated that buellolide (13) and canesolide (18) arise by catabolism of their congeneric depsidones, in the latter case with Smiles rearrangement.This publication has 4 references indexed in Scilit:
- Depsidone synthesis. Part 14. The total synthesis of psoromic acid: isopropyl ethers as useful phenolic protective groupsJournal of the Chemical Society, Perkin Transactions 1, 1979
- Depsidone synthesis. Part 13. The total synthesis of variolaric acidJournal of the Chemical Society, Perkin Transactions 1, 1979
- Chemistry and crystal structure of leprolomin, a novel diphenyl ether from the lichen Psoroma leprolomumAustralian Journal of Chemistry, 1978
- Depsidone synthesis. V. The chemistry of psoromic acid: a reinvestigationAustralian Journal of Chemistry, 1976