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Open AccessArticle

Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core

1
Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, Eötvös utca 6, Hungary
2
MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, H-6720 Szeged, Eötvös utca 6, Hungary
3
Department of Microbiology, University of Szeged, 6726 Szeged, Közép fasor 52, Hungary
4
Interdisciplinary Centre of Natural Products, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary
*
Author to whom correspondence should be addressed.
Academic Editors: Antal Csámpai, Panayiotis A. Koutentis and Antonio Massa
Molecules 2020, 25(1), 21; https://doi.org/10.3390/molecules25010021
Received: 22 November 2019 / Revised: 5 December 2019 / Accepted: 16 December 2019 / Published: 19 December 2019
(This article belongs to the Special Issue Synthesis and Structure of Heterocyclic and Organometallic Compounds)
A library of 1,2-aminoalcohol derivatives with a neoisopulegol-based octahydrobenzofuran core was developed and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The allylic chlorination of (+)-neoisopulegol, derived from natural (–)-isopulegol followed by cyclization, gave the key methyleneoctahydrobenzofuran intermediate. The stereoselective epoxidation of the key intermediate and subsequent oxirane ring opening with primary amines afforded the required 1,2-aminoalcohols. The ring closure of the secondary amine analogues with formaldehyde provided spiro-oxazolidine ring systems. The dihydroxylation of the methylenetetrahydrofuran moiety with OsO4/NMO (4-methylmorpholine N-oxide) resulted in the formation of a neoisopulegol-based diol in a highly stereoselective reaction. The antimicrobial activity of both the aminoalcohol derivatives and the diol was also explored. View Full-Text
Keywords: neoisopulegol; octahydrobenzofuran; 1,2-aminoalcohol; chiral catalyst; antimicrobial activity neoisopulegol; octahydrobenzofuran; 1,2-aminoalcohol; chiral catalyst; antimicrobial activity
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MDPI and ACS Style

Bamou, F.Z.; Le, T.M.; Volford, B.; Szekeres, A.; Szakonyi, Z. Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core. Molecules 2020, 25, 21.

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