620598-21-2Relevant articles and documents
A Modular Formal Total Synthesis of (±)-Cycloclavine
Netz, Natalie,Opatz, Till
, p. 1723 - 1730 (2016/03/01)
Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence. (Chemical Equation Presented).
One-pot enantioselective synthesis of tryptophan derivatives via phase-transfer catalytic alkylation of glycine using a cinchona-derived catalyst
Todd, Robert,Huisman, Matthew,Uddin, Nazim,Oehm, Sarah,Hossain, M. Mahmun
, p. 2687 - 2691 (2013/01/15)
Tryptophans are building blocks for many natural products. This paper describes the enantiospecific synthesis of ring-A substituted tryptophan derivatives from commercially available gramines using chiral phase-transfer conditions. This one-pot reaction avoids protecting/deprotecting the indolylic nitrogen of gramine by choosing a chemoselective quaternization reagent, 4-(trifluoro-methoxy)benzyl bromide, to produce an electrophilic salt intermediate, which is subsequently alkylated in good yield with high enantiomeric excess. Georg Thieme Verlag KG Stuttgart · New York.
Somatostatin analogue compounds
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Page 21, (2010/11/30)
Compounds having somatostatin activity of the following Formula I, 1wherein, R1 is aryl, substituted-aryl, and aryl-(lower-alkyl)-; R2 is lower alkyl, amino substituted lower alkyl, -carboxy-(lower-alkyl), -carbamic acid-(lower-alkyl) and -carboxy-(lower-alkyl)-aryl; and R3 and R4 are independently, lower-alkyl, aryl, substituted-aryl, (substituted-aryl)-(lower-alkyl)-, heteroaryl, (heteroaryl)-(lower-alkyl)-, substituted-heteroaryl, (substituted heteroaryl)-(lower-alkyl)-, heterocyclic, heterocyclic-(lower-alkyl)-, substituted-heterocyclic, (substituted-heterocylic)-(lower alkyl)-, -carboxy-(lower-alkyl), and -carboxy-(lower-alkyl)-aryl; or a pharmaceutically acceptable, ester, ether, or salt thereof; methods for their use; and preparation.
Application of a novel design paradigm to generate general nonpeptide combinatorial scaffolds mimicking beta turns: Synthesis of ligands for somatostatin receptors
Chianelli, Dona,Kim, Yong-Chul,Lvovskiy, Dmitriy,Webb, Thomas R.
, p. 5059 - 5068 (2007/10/03)
Nonpeptide compounds that mimic bioactive peptides are desirable for a number of clinical indications. We report a new practical method for the design of scaffolds exhibiting drug-like properties that are suitable for the display of peptide pharmacophores
Methodology for the efficient synthesis of 3,4-differentially substituted indoles. Fluoride ion-induced elimination-addition reaction of 1-triisopropylsilylgramine methiodides
Iwao, Masatomo,Motoi, Osamu
, p. 5929 - 5932 (2007/10/02)
1-Triisopropylsilylgramine methiodide reacted smoothly with a variety of nucleophiles in the presence of tetrabutylammonium fluoride to give 3-substituted indoles. The 3,4-disubstituted indoles were efficiently synthesized by sequential use of 4-selective lithiation of 1-triisopropylsilylgramine and this new substitution reaction.