Melleins

Phomopsis sp. strain endophytes of the medicinal plant Erythrina crista-galli continue to yield novel compounds (Table 1). New phenyl-propane, pyronol, benzoic acid, phenylpyran, macrocyclic, and alkene compounds were discovered, as well as the known compounds clavatol, 4-hydroxymellein, mellein, mevalonolactone, mevinic acid, nectriapyrone, phomol, scytalone, and tyrosol. The new compounds were phomopy-ronol (101), 3-phenylpropane-l,2-diol (102), 4-(2,3-dihydroxypropoxy) benzoic acid (103), 2-(hydroxymethyl)-3-propylphenol (104), 2-... 

Mellein, 6-methoxy, (-) Rt C024 Mellein, 6-methoxy ppci24 j (.DCi93 Methionine Ppci54 Methylamine Rt 3.80 " ... 

Joan Frances Brennecke, Zulema K. Lopez-Castillo, and Berlyn Rose Mellein... 

Berlyn Rose Mellein received her BS in chemical engineering at the University of California, Santa Barbara, in 2003, before joining the graduate program at the University of Notre Dame. She earned her MS in chemical engineering in 2007 and anticipates completion of her PhD degree in 2008. 

Berlyn Rose Mellein Department of Chemical and Biomolecular Engineering University of Notre Dame Notre Dame, Indiana... 

Universitat-Gesamthochschule Paderbom Warburger StraBe 100 D-33098 Paderborn Telefon (05251) 60-2172 Isosclerone Mollisin Patulin Penicillic acid Mycorrhizin A Aurantiogliodadin (-)-3,4-Dihydro-6,8-dihydroxy-3-methylisocoumarin Epicorazine A Oosporein Verrucarin A Verrucarin B Mellein Methylmellein... 

Flight Initiation Pheromones. The mating flights of many species of carpenter ants are initiated by male mandibular gland secretions (148). These chemical stimulators of female flight appear to constitute relatively species-specific blends of compounds that are dominated by compounds such as 2,4-dimethyl -2-hexenoic acid, methyl 6-methyl salicylate (XXXIV), methyl anthranilate (XXXIX), 10-methyldodecanoic acid, and the lactone mellein (XL) (149, 150). Recently, the sex-specific blend of... 

Sundaram, J., Mellein, B.R. and Mitragotri, S. (2003) An experimental and theoretical analysis of ultrasound-induced permeabilization of cell membranes. Biophys. J. 84, 3087-3101. 

Dihydro-8-hydroxy-3-methylisocoumarin (Ar4) (mellein) is the trail pheromone of the ants Formica rufa225 and Lasius (Dendrolasius) fuliginosus226 It is also the male pheromone of the moth Aphomia sociella227 and a... 

Mellein pratense, T. spp., Trigonella spp., Vicia faba (Fabaceae) Ipomoea pes-caprae COX (PGS) (340)... 

The reaction of ort/zo-metallated tertiary benzamides with epoxides affords a mixture of anti and syn alcohols which on lactonisation gives the dihydroisocoumarin as a single diastereomer. Using (5)-(+)-propylene oxide it was possible to synthesise the fungal metabolite (5)-(+)-mellein 29 <06SL873>. 

Esterification of 5-hydroxyhex-2-enals with diketene is followed by a Michael addition and an aldol reaction in a one-pot stereoselective synthesis of hexahydroisocoumarins (Scheme 35). Aromatisation affords dihydroisocoumarins such as (-)-mellein <07T1074, 07T1281>. 

Bidentate base. The chiral lithium amide of (S)-l has been used to generate the anion of the ethyl o-toluate 2 and as a chiral complcxing agent in reaction of the anion with acetaldehyde to give optically active mellein methyl ether (3) in 53% optical yield. Optical yields are markedly lower when a chiral base similar to 1 but lacking the OCH, group is used. 

A recent synthesis of mellein involves a Diels-Alder reaction, which gives the expected 1,2,3-trisubstituted benzene derivative... 

Trifluoroacetic acid catalysed claisen rearrangement also provides another route to mellein 32 as shown below. 

Mellein [( )-3,4-dihydro-8-hydroxy-3-methyl-2-henzopyran-l-one, 8-hydroxy-3-methylisochroman-l-one] [1200-93-7] M 178.2, m 37-39 , 39 , pKsst 9.5. Purify it by... 

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