Jatropha gossypiifolia

Diels-Alder reaction of the furan derivative 148 with homochiral bicyclic enone 149 is the key step [56] in the total synthesis of the diterpenes jatropho-lone A and B, 151 and 152, respectively, isolated from Jatropha gossypiifolia L [57], Initial efforts to carry out the cycloaddition between 148 and 149 under thermal or Lewis-acid conditions failed due to diene instability. Application of 5kbar of pressure to a neat 1 1 mixture of diene and dienophile afforded crystalline 150 with the desired regiochemistry (Scheme 5.23). Subsequent aromatization, introduction of the methylene group, oxidation and methylation afforded (-l-)-jatropholones 151 and 152. 

Phorbol and its Relatives.—Jatrophone (114) is a macrocyclic diterpenoid tumour-inhibitor which has been isolated from Jatropha gossypiifolia (Euphorbiaceae). The structure was proven by Z-ray analysis of a cyclization product obtained with HBr in glacial acetic acid. Bertyadional (115) has been isolated from a Bertya species n.m.r. studies defined a large fragment of the molecule. The trienedione, which was reduced with zinc and acetic acid, underwent an isomerization in hot aqueous pyridine in which the 4(10) double bond was shifted to the 1(2) position. 

Extracts of Jatropha gossypiifolia L. and related species have been used for many years in Costa Rica to treat cancerous growths. An alcoholic extract of the roots of Jatropha gossypiifolia (supplied by J. A. Saenz Renauld of the University of Costa Rica) was found by CCNSC to show inhibitory activity against four standard animal tumor systems (sarcoma 180, Lewis lung carcinoma, and lymphocytic leukemia P-388 in the mouse, and the Walker 256 intramuscular carcinosarcoma in the rat) and in vitro... 

C20H24O3, Mr 312.41, needles, mp. 152-153°C, [a] +292° (C2H5OH). A macrocyclic diterpene of the jatro-phane type from Jatropha gossypiifolia (Euphorbia-ceae). In animal experiments J. is active against various types of cancer. Ifi-Hydroxy-J. (C20H24O4, Mr 328.41) and 2a-hydroxy-J. tom the roots of the same... 

The name jatrophane stems from Jatropha gossypiifolia (Euphorbiaceae) whieh was found to contain the antineoplastic and antileukemic (+)-jatrophone. Various differently substituted jatrophanes are isolated from Euphorbiaceae, such as the esulones from Euphorbia esula and the euphomines from E. helioscopia and E. maddeni. 

Kupchan SM, Sigel CW, Matz MJ, Saenz Renauld JA et al. 1970 Tumor inhibitors. LIX. Jatrophone, a novel macrocyclic diterpenoid tumor inhibitor from Jatropha gossypiifolia. J Am Chem Soc 92 4476-4477... 

Jatrophone (LXXV) a new diterpenoid ketone of novel structure, which possesses tumour inhibitory properties, has been isolated from Jatropha gossypiifolia. Its structure has been determined by spectroscopic analysis of... 

Jatrophone Jatropha elliptica, J. gossypiifolia Glu-R (DJNA) [antitumour,... 

Jatropha curcas, J. gossypiifolia, J. Weberbaueri SV, MCMV Virucidal [11]... 

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