3-Hydroxy-4-methyl-2-methylamino-6-octenoic

Ecample Miller and Rich investigated the conformational consequences of substitutions on an amino acid in cyclosporin A, an important immunosuppressive drug. One of the amino acids in this cyclic undecapeptide is (2, 3r, 4r, 6e)-3-Hydroxy-4-methyl-2-(methylamino)-6-octenoic acid (MeBmt). It is essential for biological activity. 

This type of yvn-seleclivc aldol addition has been applied in the synthesis of the unusual L-threonine based amino acid, (2,S, 3/ ,6F)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid, of cyclosporine104, of the cyclic hexapeptide echinocandin105, and of the antibiotic ionomycin97. 

Synthesis of (25, 3R,4/ ,6 )-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid (MeBmt) 19... 

A facile, preparative-scale synthesis of (21 ,4 )-2-methyl-4-hexenal 1841, a key intermediate in the synthesis of (2S,3J ,4J ,6 )-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid (MeBmt), has been reported [1337]. The hexenal 1841 was prepared by hydrolyzing the starting amide 1838 with sulfuric acid, redudng the resulting acid 1839 with LiAlH4, and oxidizing the resulting alcohol 1840 under the Swern conditions. 

Difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-pentanoic acid 4,ll-bis[(2-Aminoethyl)amino]anthra[2,3-b]furan-5,10-diones 4(l-Anilino-podophyllotoxin derivatives 5-Aza-2 -deoxycytidine 5-Bromotetrandrine 5-Cyclohexylindolyl-2 -deoxyribose (non-natural nucleoside) 5 -Fluorosulfonylbenzoyl 5 -adenosine 5-Fluorouracil 5,5-Diphenylbarbituric acid 6-[(2S,4R,6E)-4-Methyl-2-(methylamino)-3-oxo-6-octenoic acid] cyclosporine D (PSC833) 6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid 6-Mercaptopurine 6-Prenylchrysin 6-Thioguanine 6,7-Dimethoxy-... 

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