Methyl monate

Marko et al. employed an enantioselective Noyori BINAL-H reduction in the synthesis of methyl monate C (11), the methyl ester derivative of the potent antibiotic pseudomonic acid C6 (Scheme 4.3e). The a,(3-unsaturated ketone 12 underwent the Noyori reduction with the (S)-BINAL-H reagent to give the product desired (13) in 70% yield and 95% ee. The chiral alcohol was then condensed... 

The synthesis of methyl monate C constitutes a similar example, in which the intramolecular Sakurai reaction between ketal 151 and hydroxylated allyl silane 152 gave pyrane 154, setting up two stereogenic centers, and positioning all the pyrane substituents in equatorial positions. ... 

The main volatile component of jasmin oil is benzyl acetate. However, minor components such as indole [120-72-9], cw-jasmone [488-10-8], and methyl jas-monate [1211-29-6] contribute strongly to the typical jasmin fragrance [544-549]. 

Scheme 8 Thioglycoside-based glycosidation reactions, (a) thiophile = JV-btvmosuccwimide (NBS) [35], methyl tnflate [38], dimethyl(methyIthto)sulfonium triflate (DMTST) [39], or AModo-succmiraide (NlS)-triflic acid [40]. (b) TBPA+- = tris (4-bromophenyl)ammoniumyl hexachloroanti-monate [42]. (c) mCPHA = m-chloroptrbenmic acid [43],...

Sulfoninm Diethylamino-methyl-succinimido- (hexachloroanti-monat) Ell, 355f. (S-Aminier.)... 

Methyl oxocarbonium hexafluoroanti-monate, 692-693 Methyl palmitate, 157... 

Pauli, H.H. and T.M. Kutchan (1998). Molecular cloning and functional heterologous expression of two alleles encoding (S)-N-methylcoclaurine 3 -hydroxylase (CYP80B1), a new methyl jas-monate-inducible cytochrome P-450-dependent mono-oxygenase of benzylisoquinoline alkaloid biosynthesis. Plant J. 13, 793-801. 

Cho, H.Y., Sung-Yong, H.Y., and Park, J.M. 2008. Differential induction of protein expression and benzo-phenanthridine alkaloid accumulation in Eschscholtzia califomica suspension cultures by methyl jas-monate and yeast extract. J. Microbiol. BiotechnoL, 18 255-262. 

Plant aromatic L-amino acid decarboxylases (AADCs) catalyze the initial reactions in the formation of terpenoid indole alkaloids (TIAs) such as quinine and strychnine, and benzyliso-quiuoline alkaloids (BIAs) such as morphine and codeine (Fig. 3). L-tryptophan decarboxylase (TDC) initiates TIA synthesis with the formation of tryptamine. TDC is encoded by two genes in Cola accuminata TDCl is expressed as part of a developmentally regulated chemical defense system, whereas TDC2 is induced after elicitation with yeast extract or methyl jas-monate (MI). 

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