Stereoselective alkylation of tartrate derivatives. A concise route to (+)-O-methylpiscidic acid and natural analogues.
نویسندگان
چکیده
The lithium enolate of (2S,3S,5S,6S)-dimethoxy-2,3-dimethyl-1,4-dioxane-5,6-dithiocarboxylate undergoes stereoselective mono- and/or dialkylations to afford two new stereogenic centers. The alkylation products obtained possessed a cis stereochemistry, which was confirmed by the synthesis of natural 4'-O-methylpiscidic acid dimethyl ester .
منابع مشابه
Pharmacological properties of some 3-substituted indole derivatives, a concise overview
Indole is a nitrogen-containing heterocycle. It is a very important motif in agriculture and pharmacy. Many compounds containing indole moiety has been isolated form nature. It is also an important part in natural alkaloids. Tryptophan is an amino acid which posses indole. 3-Sustituted indoles are the main group of its derivatives. Because the wide-spread application of 3-substituted indolic co...
متن کاملMacrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems.
The stereoselective synthesis of a challenging macrocyclic polyene scaffold, containing a sensitive vinyl ether motif, has been accomplished using O,C-dilithiation/selective C-alkylation, Pd-catalysed etherification and Wittig reactions as key steps. An end-game macrocyclisation strategy employed a regio- and stereoselective Stille cross-coupling using Pd(Br)(N-Succ)(AsPh3)2 (AsCat) as the prec...
متن کاملStereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)
A convergent and stereoselective synthesis of chiral cyclopentyl- and cyclohexylamine derivatives of nucleoside Q precursor (PreQ0) has been accomplished. This synthetic route allows for an efficient preparation of 4-substituted analogues with interesting three-dimensional character, including chiral cyclopentane-1,2-diol and -1,2,3-triol derivatives. This unusual substitution pattern provides ...
متن کاملSynthesis and antiviral activities of spacer-linked 1-thioglucuronide analogues of glycyrrhizin
The influenza virus infection remains a significant threat to public health and the increase of antiviral resistance to available drugs generates an urgent need for new antiviral compounds. Starting from the natural, antivirally active compound glycyrrhizin, spacer-bridged derivatives were generated with improved antiviral activity against the influenza A virus infection. Simplified analogues o...
متن کاملOne-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a carboxylic acid and cinnamaldehyde
The imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the N-isocyaniminotriphenylphosphorane (Ph3PNNC) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. The 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were comp...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 4 12 شماره
صفحات -
تاریخ انتشار 2006