Total synthesis approaches to natural product derivatives based on the combination of chemical synthesis and metabolic engineering

2007 ◽  
Vol 5 (20) ◽  
pp. 3245 ◽  
Author(s):  
Andreas Kirschning ◽  
Florian Taft ◽  
Tobias Knobloch
Keyword(s):  
Metabolic Engineering ◽  
Chemical Synthesis ◽  
Total Synthesis ◽  
Natural Product

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>

Total synthesis of the marine natural product (+)-discodermolide in multigram quantities

2007 ◽  
Vol 79 (4) ◽  
pp. 685-700 ◽  
Author(s):  
Stuart J. Mickel
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Natural Product ◽  
Clinical Evaluation ◽  
Chemotherapeutic Agents ◽  
Marine Natural Product ◽  
The Novel

The novel polyketide (+)-discodermolide was isolated in very small quantities from sponge extracts. This compound is one of several microtubule stabilizers showing promise as novel chemotherapeutic agents for the treatment of cancer. The clinical evaluation of this and similar compounds is hampered by lack of material, and at present, the only way to obtain the necessary quantities is total chemical synthesis.

Two Atropisomeric N-Methyldioncophyllines A and N-Methylphylline, their Naphthalene-Free Heterocyclic Moiety, from Ancistrocladus barteri

2003 ◽  
Vol 58 (6) ◽  
pp. 577-584 ◽  
Author(s):  
Gerhard Bringmann ◽  
Christoph Schneider ◽  
Ulrike Möhler ◽  
Robert-Michael Pfeifer ◽  
Roland Götz ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Natural Product ◽  
West African ◽  
The West ◽  
Naphthylisoquinoline Alkaloids ◽  
Crude Extracts ◽  
First Time ◽  
Heterocyclic Moiety

The West African plant Ancistrocladus barteri (Ancistrocladaceae) was investigated chemically for the first time. Besides the known naphthylisoquinoline alkaloids N-methyldioncophylline A and 7-epi-N-methyldioncophylline A (i.e. its atropo-diastereomer), a new naphthalene-free alkaloid, belonging to the ‘Dioncophyllaceae type’, was isolated. Its structure was elucidated by spectroscopic and degradative methods and confirmed by total synthesis. The new compound, named N-methylphylline, is exactly the isoquinoline “half” of both, N-methyldioncophylline A and its atropisomer. Furthermore, the related tetrahydroisoquinoline O,N-dimethylphylline, an intermediate in the chemical synthesis of N-methylphylline, was detected as a new natural product in crude extracts of A. barteri.

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>

Progress Toward The Total Synthesis Of The Marine Natural Product Karlotoxin 5

Planta Medica ◽  
2013 ◽  
Vol 79 (10) ◽  
Author(s):  
M Albadry ◽  
Y Zou ◽  
Y Takahashi ◽  
A Waters ◽  
M Hossein ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product

Total Synthesis of the Antitumor Depsipeptide FE399 and its S-Benzyl Derivative: A Macrolactamization Approach

2020 ◽  
Author(s):  
Takayuki Tonoi ◽  
Miyuki Ikeda ◽  
Teruyuki Sato ◽  
Ryo Kawahara ◽  
Takatsugu Murata ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Total Synthesis ◽  
Natural Product ◽  
Condensation Reaction ◽  
Practical Method ◽  
Equilibrium Mixture ◽  
Conformational Isomers ◽  
Single Isomer

<div>An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.</div>

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