Article 2022 · 4 atıf

Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

Polat, Ilknur, Essiz, Selcuk, Bozkaya, Ugur, Salamci, Emine

Özet

The first synthesis of 2-amino-3,4-dihydroxycyclooctane-1-carboxylic acid, methyl 6-hydroxy-9-oxo-8-oxabicyclo[5.2.1]decan-10-yl)carbamate, and 10-amino-6-hydroxy-8-oxabicyclo[5.2.1]decan-9-one starting from cis-9-azabicyclo[6.2.0]dec-6-en-10-one is de-scribed. cis-9-Azabicyclo[6.2.0]dec-6-en-10-one was transformed into the corresponding amino ester and its protected amine. Oxi-dation of the double bond in the N-Boc-protected methyl 2-aminocyclooct-3-ene-1-carboxylate then delivered the targeted amino acid and its derivatives. Density-functional theory (DFT) computations were used to explain the reaction mechanism for the ring opening of the epoxide and the formation of five-membered lactones. The stereochemistry of the synthesized compounds was deter-mined by 1D and 2D NMR spectroscopy. The configuration of methyl 6-hydroxy-9-oxo-8-oxabicyclo[5.2.1]decan-10-yl)carba-mate was confirmed by X-ray diffraction.

Anahtar Kelimeler

aminocyclitol azidolysis bicyclic 8-lactam bicyclic lactone cyclic 8-amino acids DFT BETA-LACTAMS AMINO-ACIDS

WoS Kategorileri

Chemistry, Organic

Sürdürülebilir Kalkınma Amaçları

Sağlık ve Kaliteli Yaşam

Künye

Dergi: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Yıl: 2022
Cilt: 18
Sayfa: 77-85
ISSN: 1860-5397
DOI: 10.3762/bjoc.18.7
WoS UID: WOS:000742474400001

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