An Efficient Enantioselective Synthesis of (−)-Galanthamine

Trost, Barry M.; Tang, Weiping

doi:10.1002/1521-3757(20020802)114:15<2919::aid-ange2919>3.0.co;2-n

Cited by 22 publications

(4 citation statements)

References 14 publications

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“…The cis-fused ringsystem was determined by NOESY NMR experiments. 32,33 In a few cases, the Heck product was isolated together with trace amounts of a double bond isomer. Interestingly, when conducting the Mizoroki−Heck reaction with ring ether 6e, the seven-membered carbocycle 10 is obtained as a 1:1 mixture of diastereomers.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Chiral Dihydrobenzofuran Acids Show Potent Retinoid X Receptor–Nuclear Receptor Related 1 Protein Dimer Activation

et al. 2016

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The nuclear receptor Nurr1 can be activated by RXR via heterodimerization (RXR-Nurr1) and is a promising target for treating neurodegenerative diseases. We herein report the enantioselective synthesis and SAR of sterically constricted benzofurans at RXR. The established SAR, using whole cell functional assays, lead to the full agonist 9a at RXR (pEC50 of 8.2) and RXR-Nurr1. The X-ray structure shows enantiomeric discrimination where 9a optimally addresses the ligand binding pocket of RXR.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Chiral Dihydrobenzofuran Acids Show Potent Retinoid X Receptor–Nuclear Receptor Related 1 Protein Dimer Activation

et al. 2016

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“…Furthermore, the use of carbonate rather than tertiary amine bases minimizes the problem of simple hydrogenolysis of the triflate (entry 1 vs 2, Table 2). With either dppe or dppp as ligands,22 the desired alkene 24 was isolated in 42–48 % yield which increased to 58 % with dppb 23…”

Section: Resultsmentioning

confidence: 99%

A Short and Concise Asymmetric Synthesis of Hamigeran B

Trost

Pissot‐Soldermann

Chen

2005

Chemistry A European J

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The interesting biological properties of the hamigerans wherein hamigeran B is a potent antiviral agent with low cytotoxicity to host cells make these deceptively simple looking structures challenging synthetic targets. A strategy to hamigeran B evolved wherein the three contiguous stereocenters are established ultimately from a Pd catalyzed asymmetric allylic alkylation (AAA). The latter involves an asymmetric allylation of a non-stabilized ketone enolate in 77 % yield and 93 % ee. By using this process, (S)-5-allyl-2-isopropyl-5-methyl-1-trifluoromethanesulfonyloxycyclopentene becomes available in four steps from 2-methylcyclopentanone. Introduction of the aryl unit by cross-coupling proceeded intermolecularly but failed intramolecularly. On the other hand, reductive removal of the triflate permitted a Heck reaction to effect intramolecular introduction of the aryl ring. The unusual conformational properties of this molecular architecture are revealed by the regioselectivity of the beta-hydrogen elimination in the Heck reaction and the diastereoselectivity of the reduction establishing the stereochemistry of the carbon bearing the isopropyl group. The successful route consists of 15 steps from 2-methylcyclopentanone and dimethylorcinol illustrating the efficiency of the route based upon the Pd AAA.

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“…In einer intramolekularen Heck‐Reaktion wurde das zweite, quartäre Stereozentrum mit vollständiger Diastereoselektivität aufgebaut. Angemerkt sei, dass das Produkt 48 auch als Zwischenstufe zur Synthese von (−)‐Galanthamin diente 9b. Zur Synthese von Morphin wurde 48 zunächst in das ( Z )‐Bromalken 49 überführt, bevor durch eine zweite Heck‐Cyclisierung das Phenanthren‐Gerüst mit der korrekt platzierten Doppelbindung aufgebaut wurde.…”

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The association between intensive care unit admission and subsequent depression in patients with diabetes

Davydow

Hough

Russo

et al. 2011

Int J Geriat Psychiatry

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Objective To examine whether intensive care unit (ICU) admission is independently associated with increased risk of major depression in patients with diabetes. Methods This prospective cohort study included 3596 patients with diabetes enrolled in the Pathways Epidemiologic Follow-Up Study, of whom 193 had at least one ICU admission over a 3-year period. We controlled for baseline depressive symptoms, demographics, and clinical characteristics. We examined associations between ICU admission and subsequent major depression using logistic regression. Results There were 2624 eligible patients who survived to complete follow-up; 98 had at least one ICU admission. Follow-up assessments occurred at a mean of 16.4 months post-ICU for those who had an ICU admission. At baseline, patients who had an ICU admission tended to be depressed, older, had greater medical comorbidity, and had more diabetic complications. At follow-up, the point prevalence of probable major depression among patients who had an ICU admission was 14% versus 6% among patients without an ICU admission. After multivariate adjustment, ICU admission was independently associated with subsequent probable major depression (Odds Ratio 2.07, 95% confidence interval (1.06–4.06)). Additionally, baseline probable major depression was significantly associated with post-ICU probable major depression. Conclusions ICU admission in patients with diabetes is independently associated with subsequent probable major depression. Additional research is needed to identify at-risk patients and potentially modifiable ICU exposures in order to inform future interventional studies with the goal of decreasing the burden of comorbid depression in older patients with diabetes who survive critical illnesses.

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An Efficient Enantioselective Synthesis of (−)-Galanthamine

Cited by 22 publications

References 14 publications

Chiral Dihydrobenzofuran Acids Show Potent Retinoid X Receptor–Nuclear Receptor Related 1 Protein Dimer Activation

Chiral Dihydrobenzofuran Acids Show Potent Retinoid X Receptor–Nuclear Receptor Related 1 Protein Dimer Activation

A Short and Concise Asymmetric Synthesis of Hamigeran B

The association between intensive care unit admission and subsequent depression in patients with diabetes

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