A Short, Regiocontrolled Total Synthesis of the Mold Metabolite Stipitatic Acid

1994 ◽  
Vol 47 (2) ◽  
pp. 203 ◽  
Author(s):  
MG Banwell ◽  
JR Dupuche
Keyword(s):  
Total Synthesis ◽  
Title Compound

The commercially available cis-1,2-dihydrocatechol (3) has been converted, via the σ-homo-benzoquinone (4b), into the title compound (1).

Synthesis of 14-hydroxy steroids. Total synthesis of methyl 14β-hydroxy-1,7,17-trioxo-5β,8-androstene-10β-oate and related compounds

1990 ◽  
Vol 68 (11) ◽  
pp. 1917-1922 ◽  
Author(s):  
Réjean Ruel ◽  
Pierre Deslongchamps
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Michael Addition ◽  
Title Compound ◽  
Steroid Synthesis ◽  
Related Compounds ◽  
Acetylenic Ketone

The total synthesis of the title compound 22 and methyl 14α-hydroxy-5β,13α,8-androstene-1,7,17-trioxo-10β-oate 21 isomer is reported. We also describe the 1,6-Michael addition of 2-methyl-1,3-cyclopentanedione on dienone 14 and the protic ammonium salt catalyzed intramolecular Michael addition of cyclic β-ketoester on the conjugated acetylenic ketone 13. Keywords: cardenolides, steroid synthesis, aldol, Michael addition.

3-Methoxy-2,4-di-O-methylgyrophoric acid: a novel tridepside from the lichen Parmelia subfatiscens

1981 ◽  
Vol 34 (5) ◽  
pp. 1153 ◽  
Author(s):  
JA Elix ◽  
VK Jayanthi
Keyword(s):  
Total Synthesis ◽  
Title Compound

The title compound has been isolated, characterized and the structure confirmed by total synthesis.

Approaches to the total synthesis of triterpenes. VIII. The ABC + D/E approach. Synthesis and X-ray structure determination of 1β,4a β-dimethyl-7-methoxy-1α- (7′,7′-ethyleneketal-6′,6′-dimethyl-3′-ketooctyl)-3,4,4a,9,10,10aα-hexahydro- 2(l-H)phenanthrone

1982 ◽  
Vol 60 (4) ◽  
pp. 509-513 ◽  
Author(s):  
John W. ApSimon ◽  
Rick P. Sequin ◽  
Carol P. Huber
Keyword(s):  
Total Synthesis ◽  
Single Crystal ◽  
Structure Determination ◽  
Title Compound ◽  
Trimethylsilyl Ether ◽  
Synthetic Route ◽  
X Ray ◽  
Pentacyclic Triterpenes ◽  
Ongoing Work

The title compound was made following a projected synthetic route to pentacyclic triterpenes. The key step in the route is the alkylative trapping of the enolate derived from the enol trimethylsilyl ether 8. The stereochemical consequence of this reaction is confirmed by a single crystal X-ray structure determination on 4, which although of no further utility in the projected synthesis, nevertheless served as a useful template for this determination. In this way, ongoing work in a parallel series of compounds rests on a firm stereochemical footing.

Total synthesis of (+)-swainsonine and (+)-8-epi-swainsonine

RSC Advances ◽  
2014 ◽  
Vol 4 (96) ◽  
pp. 53722-53724 ◽  
Author(s):  
Milos Trajkovic ◽  
Vesna Balanac ◽  
Zorana Ferjancic ◽  
Radomir N. Saicic
Keyword(s):  
Total Synthesis ◽  
Title Compound ◽  
Reductive Amination ◽  
Enantioselective Total Synthesis

Enantioselective total synthesis of (+)-swaisonine that hinges on a combination of organocatalyzed aldolization and reductive amination, affords the title compound in 9 steps, with 24% overall yield.

Oxidation products of arachidonic acid II. The synthesis of methyl 8R,9S,11R-trihydroxy-5Z,12E,14Z-eicosatrienoate

1980 ◽  
Vol 58 (17) ◽  
pp. 1799-1805 ◽  
Author(s):  
George Just ◽  
Corinne Luthe
Keyword(s):  
Arachidonic Acid ◽  
Total Synthesis ◽  
Title Compound ◽  
Oxidation Products ◽  
Important Intermediate

A stereospecific total synthesis of the title compound, 37, starting from diacetone glucose (9), is described. Key intermediates in the synthesis are 3-deoxy-5,6-anhydro-1,2-O-isopropylidene-glucofuranose (15), obtained in 55% yield from 9, and methyl 8-tert-butyldiphenylsilyl-9,11-O-isopropylidene-8R,9S,11R-trihydroxy-12-oxo-dodeca-5Z-enoate (33), an important intermediate in the synthesis of other oxidation products of arachidonic acid.

Total synthesis of δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine (ACV), a biosynthetic precursor of penicillins and cephalosporins

1979 ◽  
Vol 57 (11) ◽  
pp. 1388-1396 ◽  
Author(s):  
Saul Wolfe ◽  
Mark Gordon Jokinen
Keyword(s):  
Total Synthesis ◽  
Trifluoroacetic Acid ◽  
Title Compound ◽  
Biosynthetic Precursor ◽  
Oxidative Removal

The title compound has been synthesized as its disulfide by a classical route from the fully protected precursor N-BOC-S-trityl-δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine bisbenzhydryl ester. Deprotection has been achieved by oxidative removal of the trityl group with iodine, followed by removal of BOC and benzhydryl using trifluoroacetic acid. The final product is obtained in 23% overall yield from D-valine.

A Total Synthesis of Dimethyl 2,3-O-Isopropylidene-l-O-oxalyl-β-DL-ribo-hexofuran-5-ulosuronate

1975 ◽  
Vol 53 (18) ◽  
pp. 2701-2706 ◽  
Author(s):  
George Just ◽  
Karl Grozinger
Keyword(s):  
Total Synthesis ◽  
Title Compound ◽  
Catalytic Reduction ◽  
Major Product ◽  
Diels Alder ◽  
High Yield ◽  
Thermal Rearrangement ◽  
Dimethyl Acetylenedicarboxylate ◽  
Alder Adduct

The synthesis of the title compound 5 was accomplished by a high-yield thermal rearrangement of the ozonide (3) of dimethyl 5,6-O-isopropylidene-7-oxabicyclo[2.2.1]hept-2-ene-exo-5,6-diol-2,3-dicarboxylate (2a), which is obtained in 30% yield from the Diels–Alder adduct of furan and dimethyl acetylenedicarboxylate. Catalytic reduction of 5 gave methyl 2,3-O-iso-propylidene-β-DL-talofuranuronate (8) as the major product, accompanied by a small amount of the allo isomer 9.

Total Synthesis of (±)-Iso-trans-trikentrin B

1998 ◽  
Vol 51 (3) ◽  
pp. 177 ◽  
Author(s):  
John K. MacLeod ◽  
Annemarie Ward ◽  
Anthony C. Willis
Keyword(s):  
Crystal Structure ◽  
Total Synthesis ◽  
Marine Sponge ◽  
Title Compound ◽  
Compound A ◽  
X Ray ◽  
Relative Stereochemistry ◽  
Synthetic Sequence

The synthesis of the title compound, a member of a family of cyclopent[g]indoles isolated from a marine sponge, is described. Most of the synthetic sequence was developed starting from the more readily available cis-1,3-dimethylindan. An X-ray crystal structure of the indanol (24), the precursor of trans-1,3-dimethylindan, confirmed its relative stereochemistry.

scholarly journals (2R,4S,5S)-5-Hydroxy-4-methyl-3-oxohept-6-en-2-yl benzoate

IUCrData ◽  
2017 ◽  
Vol 2 (10) ◽  
Author(s):  
Valeska von Kiedrowski ◽  
Claudia God ◽  
Lena Knauer ◽  
Carsten Strohmann ◽  
Hans Preut ◽  
...  
Keyword(s):  
Natural Products ◽  
Hydrogen Bonds ◽  
Total Synthesis ◽  
Title Compound ◽  
Asymmetric Unit ◽  
Relative Configuration ◽  
Compound C

The title compound, C15H18O4, which crystallizes with two molecules in the asymmetric unit, was obtained in the course of the total synthesis of curvicollides A–C and fusaequisin A. It features the relative configuration of the Western aldol part of the natural products. In the crystal, molecules are linked by C—H...O hydrogen bonds.

scholarly journals (2R,4S,5S)-5-Methoxy-4-methyl-3-oxohept-6-en-2-yl benzoate

IUCrData ◽  
2021 ◽  
Vol 6 (9) ◽  
Author(s):  
Ann-Christin Schmidt ◽  
Lyuba Iovkova ◽  
Martin Hiersemann
Keyword(s):  
Crystal Structure ◽  
Total Synthesis ◽  
Absolute Configuration ◽  
Title Compound ◽  
Anomalous Dispersion ◽  
Allylic Alcohol ◽  
Compound C ◽  
Stereogenic Centers ◽  
The Absolute

The title compound, C16H20O4, was synthesized in the course of the total synthesis of fusaequisin A in order to verify and confirm the configurations of the stereogenic centers and to exclude the possibility of epimerization during the methylation process. The crystal structure of the title compound at 100 K has orthorhombic (P212121) symmetry. The absolute configuration was determined by anomalous dispersion and agrees with the configuration of the allylic alcohol used in the synthesis.

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