Altemaric acid

Allylzinc halides, with polymer-supported imines, 2, 398 [(7t-Allyl)zirconoxyl]carbenes, preparation, 4, 921 a-Activation, metal fluoroalkyls and fluoroaryls, 1, 735 Altemaric acid, via Alder-ene reactions, 10, 595 Alternative solvents, for green organometallic chemistry fluorous media, 12, 844 ionic liquids, 12, 846... 

Coupling of 1-alkyne 410 with 1-alkene 411, catalysed by CpRu(cod)Cl in aqueous DMF, affords the diene 414 as an ene-type product in good yield. One explanation of the reaction is the formation of the (71-al ly I )(> 2-al kync)i n termediate from the 1 -alkene and insertion of the alkyne [161]. However, formation of the ruthenacyclopentene 412, subsequent /1-elimination to form 413, and reductive elimination offer a more easily understandable mechanism. A formal synthesis of altemaric acid (415) was achieved by this reaction [162],... 

The most toxic antibiotics were altemaric acid, gliotoxin, glutinosin and mycophenolic acid, and the least toxic were griseofulvin, pencillin and streptomycin. 

Fig. 9. Synthesis of chiral altemaric acid (36) through retro Diels-Alder reaction...

An efficient synthesis of the fungal germination inhibitor Altemaric Acid required an ester which survived the ruthenium catalyst used in the formation of 103.1 [Scheme 6.103]. Since the product 103JS was also acid-sensitive, an ester... 

Brian, P.W., P.J. Curtis, H.G. Hemming, C.H. Unwin, and J.M. Wright Altemaric acid, a Biologically Active Metabolic Product of the Fungus Altemaria solani. Nature, 164, 534 (1949). 

Tabuchi, H., T. Hamamoto, S. Miki, T. Tejima, and A. Ichihara Total Synthesis of Altemaric Acid. Tetrahedron Letters, 34, 2327 (1993). 

Tabuchi, H., and A. Ichihara Stmctures and Stereochemistries of New Compounds Related to Altemaric Acid. J. Chem. Soc. (London) Perkin Trans. 1, 125 (1994). 

Brian PW, Curtis PS, Hemming HG, Unwin GH, Wright JM (1949) Altemaric Acid, a Biologically Active Metabohc Product of the Fungus Abernaria solani. Nature 164 534... 

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