Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, Eötvös utca 6, Hungary.
MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, H-6720 Szeged, Eötvös utca 6, Hungary.
Molecules. 2019 Dec 19;25(1):21. doi: 10.3390/molecules25010021.
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 OsO/NMO (4-methylmorpholine -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.
开发了一种基于 neoisopulegol 的八氢苯并呋喃核心的 1,2-氨基醇衍生物库，并将其用作手性催化剂，用于二乙基锌与苯甲醛的加成反应。（+）-neoisopulegol 的烯丙基氯化反应，来源于天然的（-）-isopulegol ，然后环化，得到关键的亚甲基八氢苯并呋喃中间体。关键中间体的立体选择性环氧化以及随后与伯胺的环氧开环反应得到所需的 1,2-氨基醇。用甲醛使仲胺类似物闭环，得到螺噁唑烷环系统。用 OsO/NMO（4-甲基吗啉氧化物）对亚甲四氢呋喃部分进行二羟化反应，在高度立体选择性的反应中形成基于 neoisopulegol 的二醇。还探索了氨基醇衍生物和二醇的抗菌活性。
