Synthesis of Phenol Derivatives from Cyclohex-2-enones Bearing an Alkyne through Lewis Acid-Catalyzed Enolization and Intramolecular Alder–Rickert Reaction

A cationic rhodium­(I) complex- or In­(OTf)₃-catalyzed synthesis of phenol derivatives from cyclohex-2-enone having an ethoxycarbonyl-substituted alkyne has been achieved. This reaction proceeds via enolization and an intramolecular Alder–Rickert reaction

Total Synthesis of <i>ent</i>-Ascospiroketal B

Ascospiroketal B was isolated from a marine-derived fungus as a structurally unique polyketide possessing a rare tricyclic core including 5,5-spiroketal-γ-lactone. An asymmetric total synthesis of <i>ent</i>-ascospiroketal B was achieved using an original synthetic route. The synthesis included the stereoselective construction of 5,5-spiroketal for ascospiroketal B and stereocontrolled construction of a quaternary asymmetric carbon by rearrangement of a trisubstituted epoxide

Amitorines A and B, Nitrogenous Diterpene Metabolites of <i>Theonella swinhoei</i>: Isolation, Structure Elucidation, and Asymmetric Synthesis

Two new nitrogenous prenylbisabolanes never before found in Lithistid sponges have been isolated from <i>Theonella swinhoei</i>. These new diterpenes, named amitorine A (<b>1</b>) and amitorine B (<b>2</b>), containing a prenylbisabolane skeleton have been characterized by spectroscopic analyses, and the relative and absolute configurations of <b>1</b> and <b>2</b> were determined by asymmetric synthesis of both diastereomers via the common bicyclic lactone <b>6</b> intermediate

Phellilane L, Sesquiterpene Metabolite of <i>Phellinus linteus</i>: Isolation, Structure Elucidation, and Asymmetric Total Synthesis

A new cyclopropane-containing sesquiterpenoid, phellilane L (<b>1</b>), was isolated from the medicinal mushroom <i>Phellinus linteus</i> (“Meshimakobu” in Japanese), a member of the Hymenochaetaceae family and a well-known fungus that is widely used in East Asia. The planar structure of <b>1</b> was determined on the basis of spectroscopic analysis. The authors achieved the first total synthesis of <b>1</b>. Our protecting group-free synthesis features a highly stereoselective one-pot synthesis involving an intermolecular alkylation/cyclization/lactonization strategy for construction of the key cyclopropane-γ-lactone intermediate. Additionally, our synthesis determined the absolute configuration of phellilane L (<b>1</b>)

Cigarette smoking is a risk factor for the onset of fatty liver disease in nondrinkers: A longitudinal cohort study

<div><p>Background</p><p>The effect of cigarette smoking on the onset of nonalcoholic fatty liver disease (NAFLD) is unclear, especially that associated with drinking small amounts of alcohol. We conducted a longitudinal study to investigate the relationship between cigarette smoking and NAFLD onset, which was stratified according to the amount of alcohol consumed.</p><p>Methods</p><p>We enrolled 7,905 Japanese subjects who had received annual health checkups more than twice between April 2003 and August 2013, 4,045 of whom met at least one of the following exclusion criteria and were excluded: (a) fatty liver at baseline; (b) hepatitis B or hepatitis C; (c) alcohol consumption (men: ≥210 g/wk; women: ≥140 g/wk); (d) change in alcohol drinking status between baseline and the study’s endpoint; (e) change in cigarette smoking habits between baseline and the study’s endpoint; or (f) current treatment with antidiabetic agents, antihypertensive agents, and/or lipid-lowering agents. The remaining 3,860 subjects (1,512 men, 2,348 women) were divided into two groups based on average alcohol consumption.</p><p>Results</p><p>After adjusting for the variables associated with metabolic disease, smoking was associated with fatty liver disease onset compared with nonsmokers in nondrinkers (adjusted hazard ratio = 1.988, 95% confidence interval 1.057–3.595; <i>p</i> = 0.034). No association was found between smoking and fatty liver disease onset in the low alcohol consumption group (men: <210 g alcohol/week; women: <140 g alcohol/week). The fatty liver disease incidence increased significantly among the nondrinkers as the number of cigarettes smoked increased (<i>p</i> = 0.001).</p><p>Conclusions</p><p>Cigarette smoking may be a significant risk factor associated with NAFLD onset in nondrinkers. These results may help clinicians to identify patients who are at a high risk of developing NAFLD and to prevent the progression of NAFLD by promoting earlier interventions that help people discontinue unhealthy lifestyle habits.</p></div

Baseline characteristics of and the incidence rate of fatty liver in the low alcohol consumption group.

<p>Baseline characteristics of and the incidence rate of fatty liver in the low alcohol consumption group.</p

Flow chart of subject selection.

<p>Abbreviations: HBV, hepatitis B virus; HCV, hepatitis C virus.</p

Association between cigarette smoking and the onset of fatty liver disease.

<p>Association between cigarette smoking and the onset of fatty liver disease.</p

Baseline characteristics of and the fatty liver disease incidence rate in the nondrinkers.

<p>Baseline characteristics of and the fatty liver disease incidence rate in the nondrinkers.</p

Univariate analysis of the risk factors associated with the onset of fatty liver disease in the low alcohol consumption group.

<p>Univariate analysis of the risk factors associated with the onset of fatty liver disease in the low alcohol consumption group.</p