Formal Synthesis of Kanamienamide

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 964-968 ◽  
Author(s):  
Tao Ye ◽  
Yang Li ◽  
Yian Guo ◽  
Zhengshuang Xu
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Asymmetric Reduction ◽  
Formal Synthesis ◽  
Wittig Olefination ◽  
Key Features

A formal total synthesis of the anticancer natural product kanamienamide has been accomplished. This communication describes two approaches to the macrocyclic core of the natural product. The key features of the route include an efficient macrolactamization, a Corey–Bakshi–Shibata asymmetric reduction, and a Stork–Zhao–Wittig olefination.

Total synthesis of Sceletium alkaloids (±)-joubertinamine, (±)-epijoubertinamine, (±)-tortuosamine and formal synthesis of (±)-mesembrine, (±)-N-formyltortuosamine

2016 ◽  
Vol 40 (11) ◽  
pp. 9432-9440 ◽  
Author(s):  
Viraj A. Bhosale ◽  
Dattatraya U. Ukale ◽  
Suresh B. Waghmode
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Formal Synthesis ◽  
Wittig Olefination

An efficient collective formal/total synthesis of Sceletium alkaloids achieved by employing the Wittig olefination–Claisen rearrangement protocol.

scholarly journals The First Total Synthesis of (±)-Methyl Salvianolate A Using a Convergent Strategy

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 999
Author(s):  
Bo Wang ◽  
Liping Wang ◽  
Ying Peng ◽  
Yiying Pang ◽  
Hesheng Xiao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Large Scale ◽  
Protecting Groups ◽  
Key Features

Herein, a convergent, practicable and first total synthesis of the natural product, (±)-methyl salvianolate A, is reported. The key features of the approach are the use of a Horner–Wadsworth–Emmons reaction and the protection of multiple hydroxyls using silyl protecting groups. The employment of the readily removable silyl protecting groups allows the synthesis of (±)-methyl salvianolate A and its derivatives on a reasonably large scale.

Stereo-Controlled Total Synthesis of Ieodomycins A and B

2014 ◽  
Vol 881-883 ◽  
pp. 57-60 ◽  
Author(s):  
Cheng Lin Zhu ◽  
Jian Ting Zhang ◽  
Shi Peng Chen ◽  
Jun Min Feng ◽  
Gao Peng Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Aldol Reaction ◽  
Asymmetric Epoxidation ◽  
Formal Synthesis ◽  
Mukaiyama Aldol ◽  
Synthetic Sequence ◽  
Key Features ◽  
Swern Oxidation ◽  
Sharpless Asymmetric Epoxidation

A highly convergent formal synthesis of Ieodomycins A and B was achieved in 7 steps. The key features involved in the synthetic sequence of Ieodomycins A and B are the Sharpless asymmetric epoxidation and the Mukaiyama aldol reaction[. The synthesis of C-3 epimer of Ieodomycins A and B was also accomplished in good yields, but now just Heptyl diene aldehyde was getted thought 4 steps. Use Geraniol as meterials to make the corresponding aldehyde (1) via Swern oxidation. Though epoxidation, Wittig reaction and HIO4oxidation to get the intermediate . Useing it though few steps, the target molecule can be getted.

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>

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>

Sign in / Sign up

Export Citation Format

Share Document