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.

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

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.

Sceptrin as a Potential Biosynthetic Precursor to Complex Pyrrole—Imidazole Alkaloids: The Total Synthesis of Ageliferin.

ChemInform ◽  
2004 ◽  
Vol 35 (36) ◽  
Author(s):  
Phil S. Baran ◽  
Daniel P. O'Malley ◽  
Alexandros L. Zografos
Keyword(s):  
Total Synthesis ◽  
Biosynthetic Precursor

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.

L-Argininium trifluoroacetate

2006 ◽  
Vol 62 (7) ◽  
pp. o3127-o3129
Author(s):  
J. Suresh ◽  
R. V. Krishnakumar ◽  
S. Natarajan
Keyword(s):  
Amino Acid ◽  
Trifluoroacetic Acid ◽  
Title Compound ◽  
Carboxylate Group ◽  
Acid Molecule ◽  
Compound C ◽  
Positively Charged

In the title compound, C6H16N4O2 +·C2F3O2 −, the amino acid exists as a zwitterionic argininium cation, with positively charged amino and guanidinium groups and a negatively charged carboxylate group. The trifluoroacetic acid molecule is deprotonated. The stoichiometry between the argininium ion and the trifluoroacetate anion is 1:1. The aggregation of argininium cations and trifluoroacetate anions is strikingly similar to those observed in the 1:2 stoichiometric analogue.

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