Total synthesis of (+)-thromboxane B2 from D-glucose. A detailed account

1981 ◽  
Vol 59 (5) ◽  
pp. 870-877 ◽  
Author(s):  
Stephen Hanessian ◽  
Pierre Lavallee
Keyword(s):  
Total Synthesis ◽  
Thromboxane B2 ◽  
Detailed Account ◽  
Target Compound ◽  
Type Symmetry

The total synthesis of thromboxane B2 from D-glucose is described, based on the recognition of hidden carbohydrate-type symmetry in the molecule. Methyl 2-deoxy-α-D-ribo-hexopyranoside was prepared from D-glucose and manipulated in such a way as to introduce C-branching at C-4 in a stereocontrolled manner. This crucial intermediate was then transformed into the target compound by adaptations of established methodology in the field.

First Total Synthesis of a Fluorinated Calystegin

2010 ◽  
Vol 65 (4) ◽  
pp. 445-451 ◽  
Author(s):  
René Csuk ◽  
Erik Prell ◽  
Stefan Reißmann ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Competitive Inhibitor ◽  
Ring Closure ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

scholarly journals Total Synthesis of the Reported Structure of Cahuitamycin A

2020 ◽  
Author(s):  
Justin Shapiro ◽  
Savannah Post ◽  
William Wuest
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Twelve Step ◽  
Target Compound ◽  
New Family ◽  
Iron Trafficking ◽  
Linear Sequence ◽  
Alternative Structure ◽  
Synthetic Target

In a 2016 screen of natural product extracts a new family of natural products, the cahuitamycins, was discovered and found to inhibit the formation of biofilms in the human pathogen <i>Acinetobacter baumannii</i>. The molecules contain an unusual piperazate residue that raises structure/function and biosynthesis questions and resemble iron-trafficking virulence factors from <i>A. baumannii</i>, suggesting a connection between metal homeostasis and biofilm-mediated pathogenicity. Here we disclose the first total synthesis of the reported structure of cahuitamycin A in a twelve-step longest linear sequence and 18% overall yield. Comparison of spectral data of the authentic natural product and synthetic target compound demonstrate that the reported structure is distinct from the isolated metabolite. Herein, we propose an alternative structure to reconcile our findings with the isolation report, setting the stage for future synthetic and biochemical investigations of an important class of natural products.

Synthesis of plantamajoside, a bioactive dihydroxyphenylethyl glycoside from Plantago major L.

Holzforschung ◽  
2006 ◽  
Vol 60 (5) ◽  
pp. 492-497 ◽  
Author(s):  
Toshinari Kawada ◽  
Yuko Yoneda ◽  
Ryuji Asano ◽  
Ippei Kan-no ◽  
Walther Schmid
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Total Synthesis ◽  
Caffeic Acid ◽  
Spectral Data ◽  
Natural Compound ◽  
Plantago Major ◽  
Target Compound ◽  
Sugar Esters ◽  
Nuclear Magnetic

Abstract The first total synthesis of plantamajoside (1), 2-(3′,4′-dihydroxylphenyl)ethyl-4-O-caffeoyl-3-O-(β-D-glucopyranosyl)-β-D-glucopyranoside, which is one of the dihydroxyphenylethyl glycosides (caffeic acid sugar esters), is described. Key intermediate 2, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-β-D-glucopyranoside was glycosylated with trichloroacetoimidoyl 2,3,4,6-tetra-O-acetyl-α-D-glycopyranoside (3) to afford plantamajoside derivative 4a, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside, in 39% yield. Plantamajoside derivative 4a was successfully converted into the target compound, plantamajoside (1), through a series of de-protective procedures. 1H- and 13C nuclear magnetic resonance (NMR) spectral data of the synthesized plantamajoside (1) were identical to those of the natural compound.

A stereospecifie, total synthesis of thromboxane B2

1977 ◽  
Vol 55 (3) ◽  
pp. 562-565 ◽  
Author(s):  
Stephen Hanessian ◽  
Pierre Lavallee
Keyword(s):  
Total Synthesis ◽  
Thromboxane B2

A stereospecific, total synthesis of crystalline thromboxane B2 from D-glucose is described.

ChemInform Abstract: TOTAL SYNTHESIS OF THROMBOXANE B2

1976 ◽  
Vol 7 (48) ◽  
pp. no-no ◽  
Author(s):  
N. A. NELSON ◽  
R. W. JACKSON
Keyword(s):  
Total Synthesis ◽  
Thromboxane B2

Synthesis and biological evaluation of palmyrolide A macrocycles as sodium channel blockers towards neuroprotection

2016 ◽  
Vol 14 (36) ◽  
pp. 8457-8473 ◽  
Author(s):  
Satish Chandra Philkhana ◽  
Suneet Mehrotra ◽  
Thomas F. Murray ◽  
D. Srinivasa Reddy
Keyword(s):  
Total Synthesis ◽  
Sodium Channel ◽  
Biological Evaluation ◽  
Detailed Account ◽  
Channel Blockers ◽  
Sodium Channel Blockers ◽  
Channel Inhibition ◽  
Synthesis And Biological Evaluation

A detailed account on total synthesis, analogue synthesis, biological evaluation and SAR of palmyrolide A macrocycles towards sodium channel inhibition is reported.

scholarly journals A chromatography-free total synthesis of a ferrocene-containing dendrimer exhibiting the property to recognize 9,10-diphenylantracene

2021 ◽  
Author(s):  
Artur Kasprzak ◽  
Monika K. Nisiewicz ◽  
Anna Maria Nowicka
Keyword(s):  
Total Synthesis ◽  
Target Compound

Molecules comprising several ferrocene residues constitute an intriguing group of compounds for various applications. Here, the total synthesis of a new example of ferrocene-containing dendrimer is presented. The target compound...

scholarly journals Total Synthesis of the Reported Structure of Cahuitamycin A

2020 ◽  
Author(s):  
Justin Shapiro ◽  
Savannah Post ◽  
William Wuest
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Twelve Step ◽  
Target Compound ◽  
New Family ◽  
Iron Trafficking ◽  
Linear Sequence ◽  
Alternative Structure ◽  
Synthetic Target

In a 2016 screen of natural product extracts a new family of natural products, the cahuitamycins, was discovered and found to inhibit the formation of biofilms in the human pathogen <i>Acinetobacter baumannii</i>. The molecules contain an unusual piperazate residue that raises structure/function and biosynthesis questions and resemble iron-trafficking virulence factors from <i>A. baumannii</i>, suggesting a connection between metal homeostasis and biofilm-mediated pathogenicity. Here we disclose the first total synthesis of the reported structure of cahuitamycin A in a twelve-step longest linear sequence and 18% overall yield. Comparison of spectral data of the authentic natural product and synthetic target compound demonstrate that the reported structure is distinct from the isolated metabolite. Herein, we propose an alternative structure to reconcile our findings with the isolation report, setting the stage for future synthetic and biochemical investigations of an important class of natural products.

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