Diastereoselective synthesis of N-acetyl-D,L-acosamine and N-benzoyl-D,L-ristosamine

N-Acyl derivatives of $\text{D}$,$\text{L}$-acosamine and $\text{D}$,$\text{L}$-ristosamine were synthesized with high stereo selectivity utilizing intramolecular Michael addition of γ- and δ-carbomoyloxy-α,β-unsaturated esters.     

[2+2] Cycloaddition of benzyne to cis,trans- and cis,cis-1,5-cyclooctadiene

The relative rates of formation of $\text{cis}$ and $\text{trans}$ [2+2]cycloadducts of benzyne to $\text{cis}$, $\text{trans}$- and $\text{cis}$, $\text{cis}$-1,5-cyclooctadiene, $\text{trans}$- and $\text{cis}$-cyclooctene are discussed and properties of the adducts (e.g., their unusual hydrogenation) are described.     

Boat-chair conformational preference of exo, exo-9-oxobicyclo[3.3.1]nonane-2,4-dicarboxylic acid

The ¹H and ¹³C nmr spectra of $\text{exo}$, $\text{exo}$-9-oxobicyclo[3.3.1]nonane-2,4-dicarboxylic acid, 3, in DMSO-d₆ or alkaline D₂O, clearly show that it exists in a $\text{boat}$-$\text{chair}$-conformation with $\text{equatorial}$ carboxyl groups, thus being the first case of $\text{boat}$-$\text{chair}$ preference of a bicyclo[3.3.1] nonan-9-one due to the presence of $\text{exo}$,$\text{exo}$-2,4- substituents.     

Highly substituted chromanols from cultures of aspergillusduricaulis

The new compounds $\text{1}$ – $\text{4}$ and $\text{8}$ have been isolated from cultures of $\text{Aspergillus}$$\text{duricaulis}$     

A new polyether toxin from Gymnodiniumbreve Davis

A new ichthyotoxic toxin was isolated from the unialgal culture of the deleterious Florida red tide organism, $\text{Gymnodinium}$$\text{breve}$ Davis (Syn. $\text{Ptychodiscus}$$\text{brevis}$), and its structure was elucidated.     

The sterepolides: new isolactaranes from stereumpurpureum

Sterepolide and dihydrosterepolide, new sesquiterpenes isolated from the fungus $\text{Stereum}$$\text{purpureum}$, are assigned structures $\text{4}$ and $\text{7}$, respectively. The assignments are based mainly on spectroscopic studies and similarities to isolactarorufin ($\text{5}$). A possible mode of biogenesis of these isolactarane type sesquiterpenes is discussed.     

Autorecycling oxidation of alcohol catalyzed by 1,3,7,9,11,12,14-heptazapentacene-2,4,8,10 (14H,3H,9H,12H)-tetraones (mixed flavins)

1,3,7,9,11,12,14-Heptazapentacene-2,4,8,10 (14$\text{H}$,3$\text{H}$,9$\text{H}$,12$\text{H}$)-tetraones (mixed flavins) were prepared by the cyclization of 1,5-dihydro-8-[N-alkyl-N-(5-nitrouracil-6-yl)-amino-5-deazaflavins with Vilsmeier reagent. The mixed flavins oxidized alcohol under neutral condition in sunlight and a remarkable autorecycling was observed.     

A new cytokinin from the fruits of zantedeschiaaethiopica

A new purine derivative with cytokinin activity was isolated from the cuckoo-pint fruits ($\text{Zantedeschia}$$\text{aethiopica}$) and identified as 6-(o-hydroxybenzylamino)-2-methylthio-9-β-D-glucofuranosylpurine $\text{1}$.     

New highly oxidized fusicoccane diterpenoids from the liverwort plagiochilaacanthophylla subsp. japonica

Four novel fusicoccane diterpenoids, fusicoplagins A, B, C, and D, have been isolated from the liverwort $\text{Plagiochila}$$\text{acanthophylla}$ subsp. $\text{japonica}$ and the structures determined by spectroscopic methods, chemical transformations, and X-ray crystallographic analysis.     

Steroidal antifeedants from the dorid nudibranch Aldisasanguineacooperi

Two steroids, 3-oxo-chol-4-ene-24-oic acid ($\text{2}$) andi ts unsaturated analog $\text{4}$ have been isolated from the dorid nudibranch $\text{Aldisa}$$\text{sanguinea}$$\text{cooperi}$, and the acid $\text{2}$ has been shown to have antifeedant properties.     

Palladium catalysed synthesis of N and S heterocyclic esters

Palladium catalysed alkoxycarbonylation of heterocyclic halides affords a simple and versatile synthesis of both $\text{N}$ and $\text{S}$ heterocyclic esters where a range of catalysts have been studied and a method to employ inexpensive inorganic bases has been found.     

Methods for stereospecific synthesis of cis or trans hydrindanones

Methods are described for the stereospecific conversion of hydrindenone 3 either to the corresponding $\text{trans}$ fused or $\text{cis}$ fused hydrindanone (1 or 2, respectively.)     

A stereocontrolled synthesis of Z and E terminal dienes from pinacol E-1-trimethylsilyl-1-propene-3-boronate

Pinacol $\text{E}$-1-trimethylsilyl-1-propene-3-boronate reacts with aldehydes to form (±)-($\text{R}$*,$\text{S}$*)-3-trimethylsilyl-4-hydroxy-1-alkenes, which can be deoxysilylated stereoselectively to either 98% $\text{Z}$ or 99% $\text{E}$ 1,3-dienes, including the separate components of the red bollworm moth pheromone.     

New tricarbocyclic cycropropanoid diterpenes from the brown alga dictyotadichotoma

The structures $\text{1}$, $\text{2}$, and $\text{3}$ have been proposed for three new diterpenes from $\text{Dictyota}$$\text{dichotoma}$ mainly on the basis of spectroscopic evidence.     

Rotational isomerism between the E and Z forms of o-substituted benzo-N-methyl hydroxamic acids in strong acid

The $\text{E}$∠$\text{Z}$ equilibrium of the cations of benzo hydroxamic acids, in mineral acid, was studied utilizing ¹H NMR spectroscopy, NOEDS and MNDO claculations     

Synthesis of (1s,5r)-karahana ether and (1s,5r)-karahana lactone,the optically active forms of unique monoterpenes wit

(1$\text{S}$,5$\text{R}$)-(-)-Karahana ether (8,8-dimethyl-2-methylene-6-oxabi-cyclo[ 3.2.1]octane) and (1$\text{S}$,5$\text{R}$)-(-)-karahana lactone (8,8-dimethyl-2-methylene-6-oxabicyclo [3.2.1]octan-7-one) were synthesized from ($\text{S}$)-3-hydroxy-2,2-dimethylcyclo-hexanone. The natural karahana lactone was shown to be almost racemic ($\text{ca}$. 1.3 % e.e.).     

Fungal metabolites 10. New chromenes from Lactarius fuliginosus fries and Lactarius picinus fries

6-Methoxy-2,2-dimethylchromene (I) and five new chromenes (II-VI) were isolated from $\text{Lactarius fuliginosus}$ and $\text{L.picinus}$ (Basidiomycetes). These unusual structures have been elucidated by spectroscopic methods. 2,2-Dimethylchromene (VII) was identified by GC-MS in $\text{L. picinus}$.     

Structures of simarinolide and guanepolide (x-ray analysis), new quassinoids from Simaba cf orinocensis

Simarinolide $\text{4a}$ and Guanepolide $\text{5a}$ are new quassinoids with a C₂₅ basic skeleton isolated from a member of the French Guyanan Simaroubaceae, Simaba cf orinocensis H.B.K. The structure $\text{4a}$ was established by spectral means and that of $\text{5a}$ by X-ray diffraction analysis. The previously known simarolide $\text{1}$ was also isolated.     

Balearone,a metabolite of the brown alga cystoseirabalearica

The isolation of a new metabolite of mixed biogenesis, balearone $\text{1}$from the brown alga $\text{Cystoscira}$$\text{balearica}$ is described. The structure was determined by an X-ray diffraction analysis.     

Plaunol A and B,new anti-ulcer diterpenelactones from Crotonsublyratus

Two new diterpenelactones named plaunol A ($\text{2}$) and B ($\text{3}$) exhibiting anti-Shay ulcer activity were isolated from Thai medicinal plant, $\text{Croton}$$\text{sublyratus}$. Structure of $\text{2}$ was determined by X-ray analysis of its $\text{p}$-bromobenzoate and structure of $\text{3}$ was deduced from the results of chemical correlation and the spectral data.