Total synthesis of antiallergic bicyclic peptide seongsanamide A

2020 ◽  
Vol 7 (13) ◽  
pp. 1658-1662
Author(s):  
Feipeng Han ◽  
Yian Guo ◽  
Tao Ye
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Absolute Stereochemistry

The first total synthesis of antiallergic depsipeptide seongsanamide A has been achieved and also the relative and absolute stereochemistry of the natural product has been confirmed.

scholarly journals Synthetic study of ravidomycin, a hybrid natural product

2000 ◽  
Vol 72 (9) ◽  
pp. 1783-1786 ◽  
Author(s):  
Keisuke Suzuki
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Amino Sugar ◽  
Antitumor Antibiotics ◽  
Ready Availability ◽  
Silyl Acetals ◽  
Gilvocarcin V ◽  
Absolute Stereochemistry

Strategies and tactics associated with the total synthesis of hybrid natural products are discussed. The target is ravidomycin (2), one of the gilvocarcin-class antitumor antibiotics with an aryl C-glycoside structure. The first total synthesis of 2, which was achieved along similar lines of that of gilvocarcin V (1), served for the determination of the relative as well as the absolute stereochemistry of 2. Also revealed was a limitation of the synthetic scheme so long as the amino sugar congener was concerned. A preliminary result is discussed on the [2+2+2] approach that relies on the ready availability of various benzocyclobutene derivatives via regioselective [2+2] cycloaddition of α-alkoxybenzynes and ketene silyl acetals.

scholarly journals New and old challenges in total synthesis. From concept to practice

2003 ◽  
Vol 75 (2-3) ◽  
pp. 209-221 ◽  
Author(s):  
S. Hanessian ◽  
Roberto Margarita ◽  
Adrian Hall ◽  
Shawn Johnstone ◽  
M. Tremblay ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Products ◽  
Stereocontrolled Synthesis ◽  
Absolute Stereochemistry

The total synthesis of dysinosin A, a novel member of the aeruginosin group of marine natural products is discussed. The stereocontrolled synthesis also confirms the proposed structure and absolute stereochemistry of the natural product.

Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A

2001 ◽  
Vol 79 (11) ◽  
pp. 1562-1592 ◽  
Author(s):  
Oren P Anderson ◽  
Anthony GM Barrett ◽  
Jeremy J Edmunds ◽  
Shun-Ichiro Hachiya ◽  
James A Hendrix ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product ◽  
Aldol Reactions ◽  
Calyculin A ◽  
Coupling Reactions ◽  
Stille Coupling ◽  
Palladium Catalyzed ◽  
Key Steps ◽  
Absolute Stereochemistry

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth–Meyers approach to the synthesis of the oxazole fragment.Key words: calyculin, marine natural product, phosphatase inhibitor, total synthesis, palladium catalyzed coupling reactions, allylboration reactions, aldol reactions, spiroketal, Cornforth–Meyers oxazole reaction.

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>

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

2019 ◽  
Author(s):  
Timothy Newhouse ◽  
Aneta Turlik ◽  
Yifeng Chen ◽  
Anthony Scruse
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Late Stage ◽  
Membered Ring ◽  
Entry Point ◽  
Ketone Reduction ◽  
Coupling Approach

<div> <p>The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI<sub>2</sub>-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class of kaurane diterpenoids.</p> </div>

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