Synthetic Studies on Biologically Active Alkaloids Starting from Lactam-type Chiral Building Blocks

ChemInform ◽  
2004 ◽  
Vol 35 (34) ◽  
Author(s):  
Naoki Toyooka ◽  
Hideo Nemoto
Keyword(s):  
Building Blocks ◽  
Biologically Active ◽  
Synthetic Studies

Synthetic studies on biologically active natural products by a chemicoenzymatic approach

Tetrahedron ◽  
1984 ◽  
Vol 40 (1) ◽  
pp. 145-152 ◽  
Author(s):  
Masaji Ohno ◽  
Yukishige Ito ◽  
Masafumi Arita ◽  
Tomoyuki Shibata ◽  
Kunitomo Adachi ◽  
...  
Keyword(s):  
Natural Products ◽  
Biologically Active ◽  
Synthetic Studies ◽  
Active Natural

scholarly journals Cellulose recycling as a source of raw chirality

2013 ◽  
Vol 85 (8) ◽  
pp. 1683-1692 ◽  
Author(s):  
Valeria Corne ◽  
María Celeste Botta ◽  
Enrique D. V. Giordano ◽  
Germán F. Giri ◽  
David F. Llompart ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Organic Carbon ◽  
Asymmetric Synthesis ◽  
Building Blocks ◽  
Biologically Active ◽  
Raw Material ◽  
Chiral Auxiliaries ◽  
High Chemical ◽  
Chiral Structure

Modern organic chemistry requires easily obtainable chiral building blocks that show high chemical versatility for their application in the synthesis of enantiopure compounds. Biomass has been demonstrated to be a widely available raw material that represents the only abundant source of renewable organic carbon. Through the pyrolitic conversion of cellulose or cellulose-containing materials it is possible to produce levoglucosenone, a highly functionalized chiral structure. This compound has been innovatively used as a template for the synthesis of key intermediates of biologically active products and for the preparation of chiral auxiliaries, catalysts, and organocatalysts for their application in asymmetric synthesis.

scholarly journals Cyclic cis-1,3-Diamines Derived from Bicyclic Hydrazines: Synthesis and Applications

Synlett ◽  
2020 ◽  
Author(s):  
Erica Benedetti ◽  
Laurent Micouin ◽  
Claire Fleurisson
Keyword(s):  
Bond Cleavage ◽  
Building Blocks ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Chemical Similarity ◽  
Active Compounds ◽  
General Overview ◽  
Biological Interest ◽  
Potential Applications ◽  
Rna Binders

AbstractCyclic cis-1,3-diamines are versatile building blocks frequently found in natural molecules or biologically active compounds. In comparison with widely studied 1,2-diamines, and despite their chemical similarity, 1,3-diamines have been investigated less intensively probably because of a lack of general synthetic procedures giving access to these compounds with good levels of chemo-, regio-, and stereocontrol. In this Account we will give a general overview of the biological interest of cyclic cis-1,3-diamines. We will then describe the synthesis and potential applications of these compounds with a particular focus on the work realized in our laboratory.1 Introduction2 Biological Relevance of the cis-1,3-Diamine Motif3 Classical Synthetic Strategies towards cis-1,3-Diamines4 N–N Bond Cleavage of Bicyclic Hydrazines: A Versatile Method to Access cis-1,3-Diamines4.1 Preparation of Five-Membered Cyclic cis-1,3-Diamino Alcohols4.2 Access to Fluorinated 1,3-cis-Diaminocyclopentanes4.3 Synthesis of cis-1,3-Diaminocyclohexitols4.4 Formation of Cyclic cis-3,5-Diaminopiperidines5 Applications of Cyclic cis-1,3-Diamines5.1 Small-Molecular RNA Binders5.2 Fluorinated 1,3-Diamino Cyclopentanes as NMR Probes6 Concluding Remarks

scholarly journals Phosphonate reagents and building blocks in the synthesis of bioactive compounds, natural products and medicines

2019 ◽  
Vol 91 (5) ◽  
pp. 811-838 ◽  
Author(s):  
Marian Mikołajczyk
Keyword(s):  
Building Block ◽  
Methyl Esters ◽  
Building Blocks ◽  
Biologically Active ◽  
Type I ◽  
Antiulcer Drug ◽  
Total Syntheses ◽  
Prostaglandin Analogues ◽  
Design And Synthesis ◽  
Neplanocin A

Abstract This account outlines the results obtained in the author’s laboratory on the application of phosphonates in the synthesis of various classes of biologically active cyclopentenones and cyclopentanones. In the first place two general methods for the synthesis of mono-, 1,2- and 1,4-dicarbonyl compounds are presented. The first is based on the use of α-phosphoryl sulfides in conjunction with the Horner reaction while in the second method the oxygenation reaction of α-phosphonate carbanion is a key step. The utility of these two approaches to 1,4-diketones as precursors of cyclopentenones was exemplified by the synthesis of dihydrojasmone and (Z)-jasmone. The use of simple phosphonates, α-phosphoryl sulfides and β- and γ-ketophosphonates as starting reagents in the synthesis of cyclopentanoid antibiotics (methylenomycin B, racemic desepoxy-4,5-didehydromethylenomycin, enantiomeric sarkomycins) is presented. The synthesis and reactivity of achiral 3-(phosphorylmethyl)cyclopent-2-enone and chiral diastereoisomeric camphor protected 3-(phosphorylmethyl)-4,5-dihydroxycyclopent-2-enones as building blocks is discussed as a platform for developing a new access to a variety of bioactive cyclopentenones. The utility and value of achiral phosphonate building block is demonstrated by the synthesis of racemic and enantiopure prostaglandin B1 methyl esters and enantiomeric phytoprostanes B1 type I and II. The range of biologically active compounds prepared from chiral diastereoisomeric cyclopentenone phosphonates is wider. Herein the total syntheses of the following target compounds are presented: enantiomeric isoterreins, natural (−)-neplanocin A and its unnatural (+)-enantiomer, anticancer prostaglandin analogues (enantiomers of TEI-9826, NEPP-11, iso-NEPP-11). The design and synthesis of racemic and four enantiopure stereoisomers of an antiulcer drug rosaprostol is also described.

Towards a sustainable production of biologically active building blocks from dye-rich wastewaters

2018 ◽  
Vol 44 ◽  
pp. S149
Author(s):  
A. Fernandes ◽  
L. Bonardo ◽  
B. Royo ◽  
M.P. Robalo ◽  
L.O. Martins
Keyword(s):  
Building Blocks ◽  
Sustainable Production ◽  
Biologically Active
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