Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol
Özet
Cyclooctene endoperoxide was used as the key compound for the synthesis of aziridinecyclooctanediol and 3-aminocyclo-octanetriol. Reduction of the cyclooctene endoperoxide, prepared by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc gave a cyclooctenediol and then benzylation of the hydroxy group yielded dibenzylated cyclooctene. Oxidation of the latter compound by OsO4/NMO followed by mesylation of the hydroxy group provided bis(benzyloxy)cyclooctane-1,2-diyl dimethanesulfonate. Reaction of the bis(benzyloxy)cyclooctane-1,2-diyl dimethanesulfonate with NaN3 gave 2-azido-3,8-bis(benzyloxy)cyclooctyl methanesulfonate. Reduction of the azide group and debenzylation to give an amine provided the new 3-aminocyclooctanetriol. Treatment of the 2-azido-3,8-bis(benzyloxy)cyclooctyl methanesulfonate with Zn/NH4Cl and debenzylation resulted in the target aziridinecyclooctanediol.
Anahtar kelimeler
Atıf için künye
Salamcı, E., & Lafzi, A. K. (2022). Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 18, 1539–1543. https://doi.org/10.3762/bjoc.18.163
BibTeX
@article{salamci2022-71002,
author = {Salamcı, Emine and Lafzi, Ayse Kilic},
title = {Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol},
journal = {BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY},
year = {2022},
volume = {18},
pages = {1539--1543},
issn = {1860-5397},
doi = {10.3762/bjoc.18.163},
url = {https://akademik.atauni.edu.tr/yayinlar/71002-efficient-synthesis-of-aziridinecyclooctanediol-and-3-aminocyclooctanetriol}
}