Asymmetric synthesis of cis -aminochromanol

Hansen, Karl B.; Rabbat, Philippe M. A.; Springfield, Shawn A.; Devine, Paul N.; Grabowski, Edward J. J.; Reider, Paul J.

doi:10.1016/s0040-4039(01)01907-4

Cited by 17 publications

(5 citation statements)

References 12 publications

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“…e synthesis of compounds 9a-f (Scheme 1) started from ring opening of methyl (R)-oxirane-2-carboxylate by commercially available 4cyanophenol (1) catalyzed by (salen)Co(III) complex [19,20] in tert-butylmethylether (TBME) at room temperature to form α-hydroxyester 2 in 81% yield following the procedure described in the literature [21]. Later, the cyano group in compound 2 was reacted with methanolic HCl to generate the intermediate 3 as HCl salt in excellent yield.…”

Section: Resultsmentioning

confidence: 99%

Substituted-Amidine Functionalized Monocyclic β-Lactams: Synthesis and In Vitro Antibacterial Profile

Zhai

Sun

et al. 2021

Journal of Chemistry

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Background. Owing to the intrinsic stability against common β-lactamases and metallo-lactamases, monobactams gathered special attention in antibiotic drug development. However, so far, aztreonam is the only monobactam approved by FDA for clinical use. We designed new derivatives of aztreonam to enhance its antibacterial efficacy. Methods. We synthesized a series of monocyclic β-lactams by modifying mainly at the C3 position of azetidinone ring. NH2 group at C3 of azetidinone was attached to thiazole and thiadiazole which in turn was linked to nitrogenous heterocyclic rings via amidine moieties. We then investigated the in vitro antibacterial activities of synthesized compounds against ten bacterial strains of clinical interest in comparison to aztreonam and ceftazidime. Results. All compounds showed improved antibacterial activities against tested strains compared to reference drugs. Compounds 14d and 14e were most potent and showed the highest potency against all bacterial strains, with MIC values ranging from 0.25 µg/mL to 8 µg/mL, as compared to aztreonam (MIC 16 µg/mL to >64 µg/mL) and ceftazidime (MIC >64 µg/mL). These compounds (14d and 14e) may be valuable lead targets against multidrug-resistant Gram-negative bacteria.

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Section: Resultsmentioning

confidence: 99%

Substituted-Amidine Functionalized Monocyclic β-Lactams: Synthesis and In Vitro Antibacterial Profile

Zhai

Sun

et al. 2021

Journal of Chemistry

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“…Hansen and co-workers utilized the Jacobsen kinetic resolution (KR) of epoxide 134 to prepare cis -aminochromanol 137 (Scheme ) . The KR proceeded in 95% ee.…”

Section: 3 Epoxidation Of Olefins231 Asymmetric Epoxidations (Includi...mentioning

confidence: 99%

Large-Scale Oxidations in the Pharmaceutical Industry

et al. 2006

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“…Several approaches have been described for the preparation of the optically pure cis ‐4‐aminochroman‐3‐ol. Hansen et al6 achieved an asymmetric synthesis in seven steps in which the absolute stereochemistry of the molecule was derived from (salen)Co III ‐catalyzed opening of methyl glycidate with phenol. The enantiomers of (±)‐ cis ‐aminochromanol were separated by formation of the diastereomeric salts with ( S )‐mandelic acid and selective crystallization of the mixture 7…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Preparation of Enantiopure Isomers of 4‐Aminochroman‐3‐ol and 1‐Amino‐1,2,3,4‐tetrahydronaphthalen‐2‐ol

et al. 2006

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Enantiomerically pure N-protected cis-4-aminochroman-3-ol (key precursor in the synthesis of novel HIV second-generation protease inhibitors), its trans isomer and both cis-and trans-1-amino-1,2,3,4-tetrahydronaphthalen-2-ol, useful chiral catalysts in organic synthesis, have been successfully prepared through a lipase-catalyzed kinetic acylation of the alcohol moiety, employing as substrates the corresponding

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Asymmetric synthesis of cis -aminochromanol

Cited by 17 publications

References 12 publications

Substituted-Amidine Functionalized Monocyclic β-Lactams: Synthesis and In Vitro Antibacterial Profile

Substituted-Amidine Functionalized Monocyclic β-Lactams: Synthesis and In Vitro Antibacterial Profile

Large-Scale Oxidations in the Pharmaceutical Industry

Chemoenzymatic Preparation of Enantiopure Isomers of 4‐Aminochroman‐3‐ol and 1‐Amino‐1,2,3,4‐tetrahydronaphthalen‐2‐ol

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