BJOC - Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

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Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

Emine Salamci and Yunus Zozik

Beilstein J. Org. Chem. 2021, 17, 705–710. https://doi.org/10.3762/bjoc.17.59

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Salamci, E.; Zozik, Y. Beilstein J. Org. Chem. 2021, 17, 705–710. doi:10.3762/bjoc.17.59

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TY  - JOUR
A1  - Salamci, Emine
A1  - Zozik, Yunus
T1  - Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols
JF  - Beilstein Journal of Organic Chemistry
PY  - 2021///
VL  - 17
SP  - 705
EP  - 710
SN  - 1860-5397
DO  - 10.3762/bjoc.17.59
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.17.59
KW  - aminocyclitols
KW  - aminocyclooctanetriol
KW  - chlorocyclooctanetriol
KW  - cyclic sulfate
KW  - cyclitols
N2  - The efficient synthesis of two new stereoisomeric 3-aminocyclooctanetriols and their new halocyclitol derivatives starting from cis,cis-1,3-cyclooctadiene are reported. Reduction of cyclooctene endoperoxide, obtained by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc yielded a cyclooctene diol followed by acetylation of the hydroxy group, which gave dioldiacetate by OsO4/NMO oxidation. The cyclooctane dioldiacetate prepared was converted to the corresponding cyclic sulfate via the formation of a cyclic sulfite in the presence of catalytic RuO4. The reaction of this cyclic sulfate with a nucleophilic azide followed by the reduction of the azide group provided the target, 3-aminocyclooctanetriol. The second key compound, bromotriol, was prepared by epoxidation of the cyclooctenediol with m-chloroperbenzoic acid followed by hydrolysis with HBr(g) in methanol. Treatment of bromotriol with NaN3 and the reduction of the azide group yielded the other desired 3-aminocyclooctanetriol. Hydrolysis of the epoxides with HCl(g) in methanol gave stereospecifically new chlorocyclooctanetriols.
ER  -

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Scholarly Works

Salamci, E.; Karavaizoglu, U. N. Stereoselective synthesis of syn-meso-cyclooctanetetraol, bromo-, and oxabicyclic amino-alcohol derivatives. Tetrahedron Letters 2023, 129, 154759. doi:10.1016/j.tetlet.2023.154759
Salamci, E.; Lafzi, A. K. Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol. Beilstein journal of organic chemistry 2022, 18, 1539–1543. doi:10.3762/bjoc.18.163
Polat, İ.; Eşsiz, S.; Bozkaya, U.; Salamci, E. Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives. Beilstein journal of organic chemistry 2022, 18, 77–85. doi:10.3762/bjoc.18.7

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