Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

Emine Salamci; Ayse Kilic Lafzi

doi:10.3762/bjoc.18.163

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

Beilstein J Org Chem. 2022 Nov 11:18:1539-1543. doi: 10.3762/bjoc.18.163. eCollection 2022.

Authors

Emine Salamci¹, Ayse Kilic Lafzi¹

Affiliation

¹ Department of Chemistry, Faculty of Sciences, Atatürk University, 25240 Erzurum, Turkey.

Abstract

Cyclooctene endoperoxide was used as the key compound for the synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol. 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.

Keywords: aminocyclitols; aminocyclooctanetriol; azides; aziridinecyclooctanediol; aziridines.

Grants and funding

The authors are indebted to the Scientific and Technological Research Council of Turkey (TUBITAK, Grant No. TBAG-110T208) and the Department of Chemistry at Atatürk University for their financial support of this work.