Biogenetic-type synthesis of (±)-dictyopterene A,an odoriferous substance obtained from brown seaweeds, Dictyopteris

Biogenetic-type synthesis of (±)-dictyopterene A ($\text{1}$) was achieved employing 1,$\text{cis}$-5-undecadien-3-ol ($\text{2}$) postulated to be a biosynthetic intermediate of $\text{1}$: this synthesis means that transformation of dictyoprolene ($\text{4}$) into dictyopterene A ($\text{1}$) was formally made.     

A novel method for the synthesis of 6,7-unsubstituted pyrrolo[3,2-d]pyrimidines

The synthesis of 2,4-dimethoxypyrrolo[3,2-$\text{d}$]pyrimidine ($\text{4}$) is described. This facile, 3-step synthesis involves the bromination of 2,4-dimethoxy-6-methyl-5-nitropyrimidine ($\text{1}$), and the subsequent conversion of compound $\text{1}$ into compound $\text{4}$.     

Stereoselective synthesis of (1R,3S)-cis-chrysanthemic acid through microbiological reduction of 2,2,5,5-tetramethyl 1,4-cyclohexanedione.

An efficient, highly stereoselective synthesis of (1$\text{R}$,3$\text{S}$)-$\text{cis}$-chrysanthemic acid 6 is described. The crucial step of this synthesis was the microbiological reduction of dione 1 into ($\text{S}$)-ketol 2.     

Synthesis of 2-isopropylfuro(2,3-b)quinolines-a new synthesis of (±)-lunacrine, (±)-lunasine and (±)-demethoxylunacrine

A new and convenient synthesis of 2-isopropylfuro-(2,3-b)quinolines ($\text{4}$) from 3-(3-methylbut-1-enyl)-2-quinolones ($\text{2}$) is described. A neat synthesis of the alkaloids (±)-lunacrine ($\text{1a}$), (±)-lunasine ($\text{12a}$) and (±)-demethoxylunacrine ($\text{1b}$) is also reported.     

Studies directed towards total synthesis of saframycin: I. A synthesis of hexahydro-1,5-imino-3-benzazocin-7,10-dione.

A short-step synthesis of $\text{2}$, the right-hand half of antibiotic saframycin ($\text{1}$), is described. The key steps of this synthesis are the acid catalyzed intramolecular double cyclization of $\text{4}$ and the oxidative demethylation of $\text{7}$ to the quinone ($\text{2}$).     

Terpenes and terpene derivatives - XV. [1 ] Synthesis of 4,8-dimethyl-2-(2-methyl-1-propenyl)--1-oxaspiro(4.5]dec-7-ene (“bisabolene oxide”)

Starting from the ketones $\text{3}$ and $\text{4}$ the synthesis of six spiro ethers with an l-oxaspiro[4.5]decane skeleton is described. Five of them, $\text{9a}$,$\text{b}$, $\text{10a}$,$\text{19}$ and $\text{19}$ represent typical partial structures of the sesquiterpenoid spiro ether $\text{1}$. The unambiguous synthesis of $\text{1}$ shows a previous assignment of “'bisabolene oxide“' to structure $\text{1}$ to be wrong.     

Asymmetric synthesis of a chroman derivative (vitamin e precursor)

Chromanmethanol $\text{2}$, a chiral intermediate for the synthesis of α-tocopherol $\text{1}$, is prepared from α-hydroxy aldehyde $\text{5}$, which is obtained by an asymmetric synthesis in over 95% ee.     

New approach to the synthesis of 6-ketosteroids via organoiron complexes.

New Methodology is described for the synthesis 6-ketosteroids, of potential value for the synthesis of β-ecdysone, $\text{via}$ tricarbonyl (4-methoxy-1-methylcyclohexadienyl) iron hexafluorophosphate $\text{1}$.     

Stereo- and regioselective methods for the synthesis of three consecutive asymmetric units found in many natural products

Regio- and stereoselective methods are described for the synthesis of compounds possessing the stereochemistry of type $\text{1a}$, $\text{1b}$, $\text{1c}$, and $\text{1d}$ from the aldehyde $\text{2}$.     

Chrysomelidial by chromyl chloride oxidation: A revised structure for gastrolactone

Non-conjugated $\text{gem}$-dialkylated alkenes were oxidized to aldehydes in the presence of α,β-unsaturated carbonyl functional groups, providing a new synthesis of $\text{1}$ and a synthesis of $\text{2}$ that led to a revised structure for gastrolactone.     

A stereocontrolled partial synthesis of 1α-hydroxy vitamin D3

A novel and efficient partial synthesis of 1α-hydroxy vitamin D₃ ($\text{6}$), starting from 7-dehydrocholesterol ($\text{1}$), is reported. The crucial step in the synthesis involves a selective Diels-Alder reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with the 6,8-diene system of previtamin D₃ ($\text{3}$), generating an adduct $\text{7}$ suitable for the stereoselective introduction of the 1α-hydroxyl group. Cycloreversion of $\text{13}$ leads to the title compound.     

Stereoselective synthesis and Diels-Alder reactions of bis-Ether 1,3 Dienes. A further test for cooperativity during cycloaddition reactions.

A stereoselective synthesis of dienes $\text{1a}$ and $\text{1b}$, using butadiene-iron tricarbonyl complexes, is described. Higher diastereoselectivity is observed during Diels-Alder reaction of $\text{1a}$ as compared with $\text{1c}$, affording good evidence for cooperativity in these cycloadditions.     

A stereocontrolled total synthesis of 2β,3β,20β-triacetoxy-5α-pregnan-6-one — A total synthesis of 20-hydroxyecdysone

The stereoselective total synthesis of 2β,3β,20β-triacetoxy-5α-pregnan-6-one ($\text{2}$) via acetylene-cation cyclization of $\text{7}$, which was readily derived from the D-ring aromatic steroid $\text{3}$, is described and this constitutes a total synthesis of 20-hydroxyecdysone ($\text{1}$).     

Nuclear analogs of β-lactam antibiotics. 7. The synthesis of 3-thia- and 3-aza-1-dethiaceph-1-em esters

The total synthesis of a 3-thia- and a 3-aza-1-dethiacepham ($\text{9}$ and $\text{16}$) are described. Neither compound possessed antibacterial activity $\text{vs}$$\text{B}$. $\text{subtilis}$. An unsaturated analog, a 3-aza-1-dethiaceph-1-em exhibited weak antibacterial activity.     

Structure and synthesis of the wing gland pheromone of the male african sugar-cane borer: Eldana saccharina (wlk.) (lepidoptera,pyralidae)

The structure of the sex attractant isolated from the wing glands of $\text{E.saccharina}$ has been determined by chemical and physical methods as $\text{trans}$-3-methyl-4-dimethylallyl- γ -lactone $\text{1}$. The synthesis of racemic $\text{1}$ is described.     

Isolation and synthesis of 1-methylisoguanosine,a potent pharmacologically active constituent from the marine sponge tenadiadigitata

A new pharmacologically active agent isolated from the marine sponge $\text{Tedania}$$\text{digitata}$ has been identified as 1-methylisoguanosine ($\text{1}$) by spectral and degradative chemical methods and synthesis from a β-D-ribofuranosylimidazole ($\text{2}$).     

New masked building block for isoprenoid polyene chain synthesis

The new building blocks $\text{2}$, $\text{3}$, and $\text{4}$ have been effecively synthesized starting from 2-hydroxymethyl-4-phenylthio-1-butene ($\text{1a}$). A convenient synthesis of retinoic acid methyl ester ($\text{9}$) using $\text{2}$ is also described.     

Synthesis of detoxininolactone derivatives and the revised absolute stereochemistry of detoxinine

A stereospecific synthesis of acetyl-$\text{L}$-valyl-detoxininolactone has been performed and the absolute stereochemistry of detoxinine has been revised to (2$\text{S}$, 3$\text{R}$, 1′$\text{S}$)-2-(2′-carboxy-1′-hydroxyethyl)-3-hydroxypyrrolidine.     

Stereoselective synthesis of (1R,3R,5S-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane

(1$\text{R}$,3$\text{R}$,5$\text{S}$)-1,3-Dimethyl]-2,9-dioxabicyclo[3.3.1]nonane $\text{1}$ has been stereoselectively synthesized based on a highly stereoselective method for the synthesis of 1,3-$\text{syn}$-polyol.     

Total synthesis of a macrocyclic spermidine alkaloid,codonocarpine

Total synthesis of codonocarpine ($\text{5}$) and its regio-isomer ($\text{1}$$\text{5}$) utilizing a new cyclization procedure is described.