First synthesis of the antifungal oidiolactone C from trans-communic acid: cytotoxic and antimicrobial activity in podolactone-related compounds.
The synthesis of the fungicide oidiolactone C starting from diterpenic trans-communic acid was carried out with an overall yield of 11.7%. The key step in the process consists of a new bislactonization reaction catalyzed by Pd(II), which gives rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid. We also carried out a study of the structure-biological activity of different natural podolactones and their synthetic precursors. Thus, the highest cytotoxic activity was found in dienic dilactones with ether-type substitutions on C-17, whereas the closure of the gamma-lactone ring is not critical for presenting a maximal antimicrobial activity.
Barrero
Alejandro F
AF
Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, Avda. Fuentenueva s/n, 18071 Granada, Spain. afbarre@goliat.ugr.es
Arseniyadis
Siméon
S
Quílez del Moral
José F
JF
Herrador
M Mar
MM
Valdivia
M
M
Jiménez
D
D
D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D002845:Chromatography; D003110:Colonic Neoplasms; D004224:Diterpenes / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D018653:Juniperus / Q000737:chemistry*; D007941:Leukemia P388; D008175:Lung Neoplasms; D009682:Magnetic Resonance Spectroscopy; D008545:Melanoma; D051379:Mice; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013696:Temperature; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000935:Antifungal Agents; D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D006576:Heterocyclic Compounds, 4 or More Rings; C461919:communic acid; C461901:oidiolactone C