Home / Articles / Glycals in enantiospecific synthesis

Glycals in enantiospecific synthesis

Alexander Genrikhovich Tolstikov 1
Alexander Genrikhovich Tolstikov
, 
Genrikh Alexandrovich Tolstikov 1
Genrikh Alexandrovich Tolstikov
1 Institute of Organic Chemistry, Ufa Scientific Centre of RAS
Published 30 November 1992
Communication , Volume 62, Issue 6, 579-601
51
Share
Cite this
GOST
 | 
Cite this
GOST
Tolstikov A. G., Tolstikov G. A. Glycals in enantiospecific synthesis // Russian Chemical Reviews. 1993. Vol. 62. No. 6. pp. 579-601.
GOST all authors (up to 50)
Tolstikov A. G., Tolstikov G. A. Glycals in enantiospecific synthesis // Russian Chemical Reviews. 1993. Vol. 62. No. 6. pp. 579-601.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC1993v062n06ABEH000034
UR - https://rcr.colab.ws/publications/10.1070/RC1993v062n06ABEH000034
TI - Glycals in enantiospecific synthesis
T2 - Russian Chemical Reviews
AU - Tolstikov, Alexander Genrikhovich
AU - Tolstikov, Genrikh Alexandrovich
PY - 1993
DA - 1992/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 579-601
IS - 6
VL - 62
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{1993_Tolstikov,
author = {Alexander Genrikhovich Tolstikov and Genrikh Alexandrovich Tolstikov},
title = {Glycals in enantiospecific synthesis},
journal = {Russian Chemical Reviews},
year = {1993},
volume = {62},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1993v062n06ABEH000034},
number = {6},
pages = {579--601},
doi = {10.1070/RC1993v062n06ABEH000034}
}
MLA
Cite this
MLA
Tolstikov, Alexander Genrikhovich, and Genrikh Alexandrovich Tolstikov. “Glycals in enantiospecific synthesis.” Russian Chemical Reviews, vol. 62, no. 6, Nov. 1993, pp. 579-601. https://rcr.colab.ws/publications/10.1070/RC1993v062n06ABEH000034.
Views / Visits / Downloads
20 / 20 / 10

Abstract

The reactions of 1,2-unsaturated sugars (glycals) are considered in this review in relation to problems of the enantiospecific synthesis of natural products, their fragments, and their analogues. The reactions occurring both with retention of the heterocycle and those carried out with the aim of obtaining open chain chiral units are discussed. It is shown that the use of glycals as a stock of chiral substances which determine the configuration of the asymmetric centres in the target products of multistage synthesis is promising. Schemes for the synthesis of natural products of different types are considered: O- and C-glycosides, nucleosides, oligosaccharides, pheromones, antibiotics, toxins, glycosphingolipids, etc. The bibliography includes 161 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
Unsaturated Sugars
Ferrier R.J.
Advances in Carbohydrate Chemistry , 1965
3.
Unsaturated sugars.
Ferrier R.J.
Advances in Carbohydrate Chemistry and Biochemistry , 1969
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
7
E. Rabinowitch
"Photosynthesis" , 1956
9.
Tolstikov Alexander Genrikhovich, Prokopenko Oleg Fedorovich, Yamilov Radik Khalyafovich, Tolstikov Genrikh Alexandrovich
Mendeleev Communications , 1991
10.
Tolstikov Alexander Genrikhovich, Prokopenko Oleg Fedorovich, Khalilov Leonard Mukhibovich, Spirikhin Leonid Vasilevich, Tolstikov Genrikh Alexandrovich
Mendeleev Communications , 1991
11.
11
T. T. Bannister
Diss. Abstr. , 1959
12.
An alternative route to furanoid and pyranoid glycals
Eitelman S.J., Hall R.H., Jordaan A.
Journal of the Chemical Society Perkin Transactions 1 , 1978
14.
Simple generation of a reactive glycosyl-lithium derivative
Lancelin J., Morin-Allory L., Sinaÿ P.
Journal of the Chemical Society Chemical Communications , 1984
15.
Highly selective metal-graphite-induced reductions of deoxy halo sugars
Fuerstner A., Weidmann H.
Journal of Organic Chemistry , 1989
16.
A new, zinc-promoted synthesis of 1,4-(1,5)-anhydro-2-deoxy-pent-(hex)-1-enitols (furanoid and pyranoid glycals)
Csuk R., Fürstner A., Glänzer B.I., Weidmann H.
Journal of the Chemical Society Chemical Communications , 1986
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
18.
Glycals from Glycosyl Chlorides
Pollon J.H., Llewellyn G., Williams J.M.
Synthesis , 1989
19.
Differentially protected ribofuranoid glycals
Cheng J.C., Hacksell U., Daves G.D.
Journal of Organic Chemistry , 1985
21.
An efficient method for the preparation of furanoid and pyranoid glycals
Ireland R.E., Wilcox C.S., Thaisrivongs S.
Journal of Organic Chemistry , 1978
22.
Convenient syntheses of substituted pyranoid glycals from thiophenyl glycosides and glycosyl phenylsulfones
Fernandez-Mayoralas A., Marra A., Trumtel M., Veyrières A., Sinaÿ P.
Tetrahedron Letters , 1989
25.
25
G. W. Robinson
J. Chem. Phys. , 1955
26.
The synthesis of the core trisaccharide of esperamicin: corroboration of the proposed structure for its rearrangement product and stabilization of the core trisaccharide domain
Halcomb R.L., Wittman M.D., Olson S.H., Danishefsky S.J., Golik J., Wong H., Vyas D.
Journal of the American Chemical Society , 1991
27.
THE MECHANISM OF THE DEHYDROBROMINATION OF TETRA-O-AGETYL-α-D-GLUGOPYRANOSYL BROMIDE
Lemieux R.U., Lineback D.R.
Canadian Journal of Chemistry , 1965
28.
Synthesis of 2-deoxy sugars from glycals
Sabesan S., Neira S.
Journal of Organic Chemistry , 1991
29.
Direct preparation of 2-deoxy-D-glucopyranosides from glucals without Ferrier rearrangement
Bolitt V., Mioskowski C., Lee S.G., Falck J.R.
Journal of Organic Chemistry , 1990
38.
A stereospecific route to 2-deoxy-.beta.-glycosides
Gervay J., Danishefsky S.
Journal of Organic Chemistry , 1991
39.
Tolstikov Alexander Genrikhovich, Savateeva Elena E, Spirikhin Leonid Vasilevich, Tolstikov Genrikh Alexandrovich
Mendeleev Communications , 1991
40.
40
A. A. Krasnovskii
Biofizika , 1960
41.
On the addition of allyltrimethylsilane to glycal acetates
Danishefsky S., Kerwin J.F.
Journal of Organic Chemistry , 1982
42.
α-C-Glycopyranosides from Lewis acid catalysed condensations of acetylated glycals and enol silanes
Dawe R.D., Fraser-Reid B.
Journal of the Chemical Society Chemical Communications , 1981
43.
Stereocontrolled routes to functionalized C-glycopyranosides
Dawe R.D., Fraser-Reid B.
Journal of Organic Chemistry , 1984
44.
C-Glycoside synthesis via glycal alkylation by olefinic derivatives
Herscovici J., Muleka K., Boumaîza L., Antonakis K.
Journal of the Chemical Society Perkin Transactions 1 , 1990
45.
Lewis acid induced homoallylic C-alkylation. A new approach to C-glycosides
Herscovici J., Delatre S., Antonakis K.
Journal of Organic Chemistry , 1987
46.
An efficient synthesis of 1-cyano-2,3-unsaturated sugars the reaction of glycals with Et2AlCN
Grierson D.S., Bonin M., Husson H., Monneret C., Florent J.
Tetrahedron Letters , 1984
47.
Cyanosugars—II
De Las Heras F.G., Felix A.S., Fernández-Resa P.
Tetrahedron , 1983
48.
The stereochemistry of conjugate addition of lithium dialkyl cuprate reagents to some carbohydrate α-enones
Yunker M.B., Plaumann D.E., Fraser-Reid B.
Canadian Journal of Chemistry , 1977
49.
Regio- and stereochemistry of cross coupling of organocopper reagents with allyl ethers: effect of the leaving group
Valverde S., Bernabe M., Garcia-Ochoa S., Gomez A.M.
Journal of Organic Chemistry , 1990
50.
Stereospecific synthesis of 1,1-dialkylglycosides
Nicolaou K.C., Hwang C.-., Duggan M.E.
Journal of the Chemical Society Chemical Communications , 1986
51.
2,3-Unsaturated -glucopyranosides: A guideline to the anomeric configurational assignment
Casiraghi G., Cornia M., Colombo L., Rassu G., Gasparri Fava G., Ferrari Belicchi M., Zetta L.
Tetrahedron Letters , 1988
52.
A simple diastereoselective synthesis of 2',3'-unsaturated aryl c-glucopyranosides
Casiraghi G., Cornia M., Rassu G., Zetta L., Fava G.G., Belicchi M.F.
Tetrahedron Letters , 1988
53.
Arylation de glycals catalysée par les sels de palladium: nouvelle synthèse de C-glycosides
54.
Palladium-catalysed arylation of peracetylated glycals, III. Crystal structure of a by-product: mechanistic implications
Bellosta V., Czernecki S., Avenel D., Bahij S.E., Gillier-Pandraud H.
Canadian Journal of Chemistry , 1990
57.
Routes to C-glycopyranosides via sigmatropic rearrangements
Tulshian D.B., Fraser-Reid B.
Journal of Organic Chemistry , 1984
58.
Claisen rearrangement of allyl esters
Ireland R.E., Mueller R.H.
Journal of the American Chemical Society , 1972
59.
The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation
Ireland R.E., Mueller R.H., Willard A.K.
Journal of the American Chemical Society , 1976
60.
Enolate Claisen rearrangement of esters from furanoid and pyranoid glycals
Ireland R.E., Thaisrivongs S., Vanier N., Wilcox C.S.
Journal of Organic Chemistry , 1980
61.
3-Acyltetramic acid antibiotics. 2. Synthesis of (+)-streptolic acid
Ireland R.E., Smith M.G.
Journal of the American Chemical Society , 1988
62.
A chiral synthesis of the left-side aldehyde for lasalocid A synthesis
Ireland R.E., McGarvey G.J., Anderson R.C., Badoud R., Fitzsimmons B., Thaisrivongs S.
Journal of the American Chemical Society , 1980
63.
Stereoselective synthesis of C-glycosyl .alpha.-amino acids
Colombo L., Casiraghi G., Pittalis A., Rassu G.
Journal of Organic Chemistry , 1991
66.
High-pressure (2+2)cycloaddition of toluene-4-sulphonyl isocyanate to glycals
Chmielewski M., KaŁuża Z., Bełżecki C., SaŁanski P., Jurczak J., Adamowicz H.
Tetrahedron , 1985
67.
[2 + 2] Cycloaddition of sulfonyl and acyl isocyanates to glycals
Chmielewski M., Kaluza Z.
Journal of Organic Chemistry , 1986
68.
Optically pure 3,4-disubstituted azetidinones from sugars
Chmielewski M., Kałuza Z., Abramski W., Grodner J., Bełzecki C., Sedmera P.
Tetrahedron , 1989
71.
Reaction of α, β-unsaturated sugar lactones with formaldoxime
Panfil I., Bełzecki C., Chmielewski M., Suwińska K.
Tetrahedron , 1989
72.
Annulated pyranosides. 4. Routes to cyclohexano and cyclopentano pyranosides from carbohydrate .alpha.-enones
Primeau J.L., Anderson R.C., Fraser-Reid B.
Journal of the American Chemical Society , 1983
76.
[4 + 2] Cycloaddition reaction of dibenzyl azodicarboxylate and glycals
Leblanc Y., Fitzsimmons B.J., Springer J.P., Rokach J.
Journal of the American Chemical Society , 1989
81.
Catalysis by mercuric ion of reactions of glycals with water
Gonzalez F., Lesage S., Perlin A.S.
Carbohydrate Research , 1975
83.
Benzyl Esters of D- and L-Arabinals as Chiral Synthons in Organic Synthesis
Tolstikov A.G., Khakhalina N.V., Spirikhin L.V.
Synthesis , 1988
84.
A convenient stereoselective synthesis of D-erythro-C18-sphingosine from galactal
Hirata N., Yamagiwa Y., Kamikawa T.
Journal of the Chemical Society Perkin Transactions 1 , 1991
86.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
87.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
88.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
92.
A route to glycals in the allal and gulal series: synthesis of the thiosugar of esperamicin A1
Wittman M.D., Halcomb R.L., Danishefsky S.J., Golik J., Vyas D.
Journal of Organic Chemistry , 1990
94.
Syntheses of supposed and real pillarose
Walker D.L., Fraser-Reid B.
Journal of the American Chemical Society , 1975
96.
Ritter-like reactions of 1,2-anhydropyranose derivatives
Gordon D.M., Danishefsky S.J.
Journal of Organic Chemistry , 1991
97.
Stereocontrolled routes to cis-hydroxyamino sugars. Part VII. A synthesis of holacosamine
Georges M., Mackay D., Fraser-Reid B.
Canadian Journal of Chemistry , 1984
99.
Total synthesis of allosamidin: an application of the sulfonamidoglycosylation of glycals
Griffith D.A., Danishefsky S.J.
Journal of the American Chemical Society , 1991
102.
C-Glycosylanthraquinone synthesis: total synthesis of vineomycinone B2 methyl ester
Tius M.A., Gomez-Galeno J., Gu X.Q., Zaidi J.H.
Journal of the American Chemical Society , 1991
103.
The synthesis of D-asperlin
Valverde S., Herradon B., Rabanal R.M., Martin-Lomas M.
Canadian Journal of Chemistry , 1987
104.
A convergent total synthesis of (−)-anamarine from d-glucose
Lichtenthaler F.W., Lorenz K., Ma W.
Tetrahedron Letters , 1987
108.
Synthesis of a marine polyether toxin, okadaic acid (3) — synthesis of segment c
Ichikawa Y., Isobe M., Masaki H., Kawai T., Goto T.
Tetrahedron , 1987
110.
Enantiospecific total synthesis of pseudomonic acids from arabinose
Fleet G.W., Gough M.J., Shing T.K.
Tetrahedron Letters , 1983
112.
Convergent synthesis of polyether ionophore antibiotics: the synthesis of the monensin spiroketal
Ireland R.E., Haebich D., Norbeck D.W.
Journal of the American Chemical Society , 1985
114.
Model studies directed toward the avermectins: A route to the spiroketal subunit
Wincott F.E., Danishefsky S.J., Schulte G.
Tetrahedron Letters , 1987
115.
The total synthesis of the aglycon of avermectin A1a
Danishefsky S.J., Armistead D.M., Wincott F.E., Selnick H.G., Hungate R.
Journal of the American Chemical Society , 1987
116.
The total synthesis of avermectin A1a
Danishefsky S.J., Armistead D.M., Wincott F.E., Selnick H.G., Hungate R.
Journal of the American Chemical Society , 1989
118.
Synthesis of the ABC ring system of brevetoxin B
Nicolaou K.C., Duggan M.E., Hwang C.K.
Journal of the American Chemical Society , 1989
119.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
120.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
121.
Tolstikov Alexander Genrikhovich, Prokopenko Oleg Fedorovich, Khalilov Leonard Mukhibovich, Spirikhin Leonid Vasilevich, Berg Arnold Arturovich, Sultanmuratova Vilina Raufovna, Tolstikov Genrikh Alexandrovich
Mendeleev Communications , 1991
122.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
123.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
125.
Synthesis of 9-deoxy-8,9-oxaprostaglandins
Kelly M.J., Newton R.F., Roberts S.M., Whitehead J.F.
Journal of the Chemical Society Perkin Transactions 1 , 1990
126.
Preparation of some novel prostanoids based on a tetrahydropyran ring system
Kelly M.J., Roberts S.M.
Journal of the Chemical Society Perkin Transactions 1 , 1991
127.
Cyclopentane-annelated pyranosides: a new approach to chiral iridoid synthesis
Hashimoto H., Furuichi K., Miwa T.
Journal of the Chemical Society Chemical Communications , 1987
129.
A highly convergent total synthesis of (+)-compactin
Keck G.E., Kachensky D.F.
Journal of Organic Chemistry , 1986
130.
A useful synthon for elaboration into iridoids and alkaloids
Mattes K.C., Hsia M.T., Richard Hutchinson C., Sisk S.A.
Tetrahedron Letters , 1977
131.
Total synthesis of (-)-specionin
Curran D.P., Jacobs P.B., Elliott R.L., Kim B.H.
Journal of the American Chemical Society , 1987
133.
The total synthesis of (-)-cryptosporin
Gupta R.B., Franck R.W.
Journal of the American Chemical Society , 1989
134.
Synthesis of Naphtho[2,3-b]pyrandiones: (?)-Cryptosporin
Brade W., Vasella A.
Helvetica Chimica Acta , 1989
135.
Enantiodivergent Total Syntheses of Nanaomycins and Their Enantiomers, Kalafungins
Tatsuta K., Akimoto K., Annaka M., Ohno Y., Kinoshita M.
Bulletin of the Chemical Society of Japan , 1985
136.
138
S. Ono
J. Chem. Soc. Japan , 1957
137.
Total syntheses of negamycin and the antipode
Shibahara S., Kondo S., Maeda K., Umezawa H., Ohno M.
Journal of the American Chemical Society , 1972
138.
Total synthesis of (+)-meroquinene
Hanessian S., Faucher A., Léger S.
Tetrahedron , 1990
142.
A synthetic route to the C4 octadienic esters of trichothecenes from D-glucose
Tulshian D.B., Fraser-Reid B.
Journal of the American Chemical Society , 1981
145.
SYNTHESES OF THE TETRAHYDROFURAN SUBUNITS OF TETRONASIN AND TETRONOMYCIN
HORI K., NOMURA K., KAZUNO H., YOSHII E.
Chemical and Pharmaceutical Bulletin , 2011
146.
Synthesis of R(+)-α-Lipoic Acid
Rama Rao A.V., Purandare A.V., Reddy E.R., Gurjar M.K.
Synthetic Communications , 1987
147.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1954
148.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
149.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
150.
152
W. Albert
Trans. Electrochem. Soc. , 1943
151.
153
1899
152.
154
Friedl.
153.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
154.
Tolstikov Alexander Genrikhovich, Yamilov Radik Khalyafovich, Prokopenko Oleg Fedorovich, Tolstikov Genrikh Alexandrovich
Mendeleev Communications , 1992
155.
A Convenient Route to 3′-Amino-3′-deoxythymidine
Motawia M.S., Wengel J., Abdel-Megid A.E., Pedersen E.B.
Synthesis , 1989
157.
Synthesis of L-3'-azido-3'-deoxythymidine (L-AZT) and its stereoisomers
Wengel J., Lau J., Pedersen E.B., Nielsen C.M.
Journal of Organic Chemistry , 1991