Short Synthesis of 3-(Hydroxymethyl)xylitol and Structure Revision of the Anti-diabetic Natural Product from Casearia esculenta

2013 ◽  
Vol 15 (21) ◽  
pp. 5610-5612 ◽  
Author(s):  
Ruomeng Wang ◽  
Michael N. Paddon-Row ◽  
Michael S. Sherburn
Keyword(s):  
Natural Product ◽  
Structure Revision ◽  
Short Synthesis

A Short Synthesis of (+)-Brefeldin C via Enantioselective Radical Hydroalkynylation

2019 ◽  
Author(s):  
Lars Gnägi ◽  
Severin Vital Martz ◽  
Daniel Meyer ◽  
Robin Marc Schärer ◽  
Philippe Renaud
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Oxidation State ◽  
Single Step ◽  
Radical Process ◽  
Target Molecule ◽  
Short Synthesis ◽  
The One

<div><div><div><div><p>A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows to achieve a high trans diastereoselectivity during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis require six product purifications and it provides (+)-brefeldin C in 18% overall yield.</p></div></div></div></div>

scholarly journals Synthesis, Structure Revision, and Absolute Configuration of (+)-Didemniserinolipid B, a Serinol Marine Natural Product from a Tunicate Didemnum sp.

ChemInform ◽  
2003 ◽  
Vol 34 (3) ◽  
Author(s):  
Hiromasa Kiyota ◽  
Darren J. Dixon ◽  
Christine K. Luscombe ◽  
Stephan Hettstedt ◽  
Steven V. Ley
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
Marine Natural Product ◽  
Structure Revision

Synthesis, Structure Revision, and Absolute Configuration of (+)-Didemniserinolipid B, a Serinol Marine Natural Product from a TunicateDidemnumsp.

2002 ◽  
Vol 4 (19) ◽  
pp. 3223-3226 ◽  
Author(s):  
Hiromasa Kiyota ◽  
Darren J. Dixon ◽  
Christine K. Luscombe ◽  
Stephan Hettstedt ◽  
Steven V. Ley
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
Marine Natural Product ◽  
Structure Revision

scholarly journals Synthesis-Guided Structure Revision of the Sarcodonin, Sarcoviolin, and Hydnellin Natural Product Family

2011 ◽  
Vol 76 (4) ◽  
pp. 1013-1030 ◽  
Author(s):  
David W. Lin ◽  
Takeshi Masuda ◽  
Moritz B. Biskup ◽  
Jonathan D. Nelson ◽  
Phil S. Baran
Keyword(s):  
Natural Product ◽  
Product Family ◽  
Structure Revision

Two for One: Structure Revision of the Marine Sesterterpene Tetronic Acid Strobilinin to (8Z,13E,20Z)-Strobilinin and (8E,13Z,20Z)-Strobilinin

1994 ◽  
Vol 47 (5) ◽  
pp. 933 ◽  
Author(s):  
R Davis ◽  
RJ Capon
Keyword(s):  
Natural Product ◽  
Spectroscopic Analysis ◽  
Marine Natural Product ◽  
Geometric Isomers ◽  
Tetronic Acid ◽  
Naturally Occurring ◽  
Structure Revision ◽  
Single Compound ◽  
The Absolute ◽  
Absolute Stereochemistry

A reinvestigation of the known marine natural product strobilinin has revealed it not to be a single compound (2), but to consist of two naturally occurring geometric isomers, neither of which corresponds to the structure originally assigned. These isomers, (8E,13Z,20Z)- strobilinin (10) and (8Z,13E,20Z)-strobilinin (11), were resolved, characterized and identified as their respective acetate derivatives (6) and (7), and their structures assigned by spectroscopic analysis. It would appear that the absolute stereochemistry of the strobilinins is very likely opposite to that of co-occurring variabilin (1).

Photo-oxygenation of Phytol and the Structure Revision of Phytene-1,2-diol from Artemisia annua to Phytene-1-ol-2-Hydroperoxidek

2002 ◽  
Vol 2002 (1) ◽  
pp. 30-33 ◽  
Author(s):  
Ho-Fai Wong ◽  
Geoffrey D. Brown
Keyword(s):  
Double Bond ◽  
Singlet Oxygen ◽  
Natural Product ◽  
Spectral Properties ◽  
Artemisia Annua ◽  
Type Reaction ◽  
Structure Revision

Photo-oxygenation of racemic phytol has yielded two secondary allylic hydroperoxides and an endoperoxide hemi-acetal, which are the expected products from the “ene-type” reaction of singlet oxygen with the tri-substituted double bond in phytol. Spectral properties for one of the diastereoisomers of phytene-1-ol-2-hydroperoxide obtained from synthesis are shown to be identical with those of a natural product previously reported from Artemisia annua, which, it is concluded, was wrongly assigned as phytene-1,2-diol.

scholarly journals Total Synthesis of Nine Longiborneol Sesquiterpenoids Using a Functionalized Camphor Strategy

2021 ◽  
Author(s):  
Robert F. Lusi ◽  
Goh Sennari ◽  
Richmond Sarpong
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Strategy Development ◽  
Topological Complexity ◽  
Efficient Synthesis ◽  
Short Synthesis ◽  
Synthesis Routes ◽  
The 1960S

<p>Natural product total synthesis inspires strategy development in chemical synthesis. In the 1960s, Corey and coworkers demonstrated a visionary preparation of the terpenoid longifolene, using “strategic bond analysis” to craft a synthesis route. This approach proposes that efficient synthesis routes to bridged, polycyclic, structures should be formulated to introduce the bulk of the target’s topological complexity at a late stage. In subsequent decades, similar strategies have proved general for the syntheses of a wide variety of bridged, polycyclic molecules. Here, we demonstrate that an orthogonal strategy, which utilizes a topologically complex bicyclo[2.2.1] starting material accessed through a scaffold rearrangement of (<i>S</i>)-carvone, leads to a remarkably short synthesis of the longifolene-related terpenoid longiborneol. We also employ a variety of late-stage C–H functionalization tactics in divergent syntheses of many longiborneol congeners. Our strategy should prove effective for the preparation of other topologically complex natural products that contain the bicyclo[2.2.1] framework.</p>

Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via Late- Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin

2019 ◽  
Author(s):  
Gabor Zoltan Elek ◽  
Kaur Koppel ◽  
Dzmitry Zubrytski ◽  
Nele Konrad ◽  
Ivar Järving ◽  
...  
Keyword(s):  
Natural Product ◽  
Histone Deacetylase ◽  
Late Stage ◽  
Stereoselective Synthesis ◽  
Cyclopropane Ring ◽  
Zinc Binding ◽  
Ring Cleavage ◽  
Inhibitory Peptides ◽  
Short Synthesis ◽  
The Common

We present a unified step-economical strategy to access histone deacetylase inhibitory peptides, based on late-stage installation of zinc-binding functionalities via the cleavage of the strained cyclopropane ring in the common pluripotent cyclopropanol precursor. The efficacy of the proposed diversity-oriented approch has been validated by short stereoselective synthesis of a natural product chlamydocin and a number of its analogs.<br>

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