Amino cyclitols synthesis

In a related contribution O Brien described the AA on styrenes and converted the amino alcohols into enantiopure diamines by using a reaction strategy similar to Janda s [83], Further synthetic applications of the AA include a new access to Evans chiral oxazolidinones [84], the enantioselective synthesis of a-amino ketones from silyl enol ethers [85], the stereoselective synthesis of cyclohexyl norstatine [86], and a route towards amino cyclitols by aminohydroxy-lation of dienylsilanes [87]. 

Fabris F, Collins J et al (2009) Investigation of steric and functionality limits in the enzymatic dihydroxylation of benzoate esters. Versatile intermediates for the synthesis of pseudo-sugars, amino cyclitols, and bicyclic ring systems. Org Biomol Chem 7 2619-2627... 

The di(benzyloxy)cyclohexene (9) mentioned above has also been used to synthesize racemic deoxyinosamine, deoxyinosadiamine, and inosamine derivatives via the unsaturated inosamine derivatives (16) and (17) Scheme 5 illustrates the basic sequences that were applied to both isomers. The same group has similarly prepared racemic amino-cyclitols from 3-benzyloxycyclohexene, and 3-methoxycyclohexene was used for a synthesis of the peracety-late d DL - 2,5 - diamino -2,3,5- trideoxy-4 -0-5-N- dimethyl - ch iro - inositol (18). Base-catalysed cyclization of the substituted diones (19) gave the corresponding cyclitols (20), which were then used to prepare other 2,l -substituted cyclitols including mono- and di-amino-cyclitols, e.g., (21). ... 

Reviews have appeared on the synthesis of aminoglycoside antibiotics, and on the formation of new aminocyclitol antibiotics by mutants of amino-cyclitol-producing organisms fed with aminocyclohexanol or related subunits. The structures of eight minor components of the nebramycin complex elaborated by Streptomyces tenebrarius have been elucidated besides neamine and related pseudo-disaccharides, the new components are pseudo-trisaccharides related to kanamycin B, and the 3 -hydroxy analogue of the principal component of the complex, apramycin (see Vol. 10, p. 130). ... 

The total synthesis of the alkaloid (+)-lycoricidine from amino cyclitol 91, prepared from bromobenzene by microbial oxidation has been reported." ... 

The synthesis of amino-cyclitols related to Hygromycin A are covered in Chapter 19. 

Hudlicky T, Olivo HF, Mckihhen B. Microhial oxidation of aromatics in enantiocontrolled synthesis. 3. Design of amino cyclitols (exo-nitrogenous) and total synthesis of... 

R. Ahluwalia, S. J. Angyal, and B. M. Luttrell, Cyclitols. XXXI. Synthesis of amino- and nitro-cyclopentanetetrols, Aust. J. Chem., 23 (1970) 1819-1829. 

So far, a number of ways have been proposed for the chemical synthesis of carbohydrates, employing the following as substrates 1, acetylenes 2, alkenes 3, dihydropyrans 4, cyclitols 5, dienes and 6, amino acids. All of these processes, however, require eomplicated synthetic procedures of 5 to 10 (or more) steps for the complete synthesis of monosaccharides, and the final yields of diserete carbohydrates are very low. In contrast, the synthesis of formose from formaldehyde proceeds directly with a high yield this could constitute a promising, economical supply of carbohydrates on an industrial scale. 

During the past nine years the subject of total synthesis of sugars and cyclitols has been vividly developed. The discovery of a large number of unusual sugars in nature—deoxy, amino, branched chain sugars (many of them components of antibiotics)—made their synthesis attractive. On the other hand, improvements in organic reagents and synthetic methods allowed a return to older preparations which could be now better performed. Finally, some synthetic ideas already described in this series, in the first chapter of the volume on the total synthesis of carbohydrates, are further expanded. 

The known 7-e carboxylic acid 506, obtained by the condensation of acrylic acid with furan, was used as a substrate for synthesis of validamine, (510) a component of validamycin antibiotics. The treatment of 506 with hydrogen peroxide in formic acid gave the tricyclic compound 507, which after reduction and hydrolysis afforded cyclitol. Treatment of 508 with 2,2-dimethoxy-propane in the presence of an acid gave a mixture of diisopropylidene derivatives in which compound 509 was predominant. Introduction of an amino group, by way of a tosyl ester and azide displacement, followed by hydrogenation and hydrolysis, completed the synthesis of DL-val-... 

Istamycin A (4) and istamycin B (5) have been isolated from the culture broth of Streptomyces tenjimariensis, and sannamycin A (identical with istamycin A) and sannamycin B (6) from the culture broth of Streptomyces sannan-ensis- these are likewise 1,4-diamino-cyclitol ot-glycosides of 6-A -methyl-purpurosamine C. (The synthesis of this amino-sugar is mentioned in Chapter 8.) Derivatives of the amino-sugar and cyclitol constituents of fortimicin B have been prepared by benzyloxycarbonylation and alcoholysis of the antibiotic. ... 

Anhydromaltose has been converted to the pseudo-disaccharides (25) containing 3-amino-3-deoxy-epz-inositol or 1-amino-l-deoxy-l-L-myo-inositol via the 6-deoxy-6-nitromaltose derivative (26). The branched-chain unsaturated 6-nitro-sugar (27), prepared conventionally from D-glucose, yielded isomeric dithianyl adducts which were similarly cyclized to give the nitro-cyclitols (28) and (29), of interest as potential intermediates for the synthesis of tetrodo-... 

A highly stereoselective synthesis of racemic amino-bromo-cyclitols from the Diels-Alder adduct derived by reaction of furan with cyanovinyl acetate (Vol. 23, p.I83) has been reported. ... 

Full details on new methods for the synthesis of A/-alkyl- and N,lV-dialkyl-derivatives of 2-amino-2-deoxy-D-glucose (cf. Vol.26, Ch.9, ref.36) have been reported. Four 1,4-imino-linked carbadisaccharides, e.g. 63, were synthesized by reaction of methyl 4-amino-4-deoxy-a-D-glucoside with a cyclitol epimine. The 1,6-linked di-mnnno-analogue 64 was obtained similarly by reaction of methyl 6-amino-6-deoxy-a-D-glucoside with a cyclitol epoxide, and was found to be an inhibitor of Jack bean a-D-mannosidase. ... 

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