Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products

2021 ◽  
Author(s):  
Rebekah G. Reynolds ◽  
Huong Quynh Anh Nguyen ◽  
Jordan C. T. Reddel ◽  
Regan J. Thomson
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Induction ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis

This review highlights strategies for the enantioselective total synthesis of cyclolignan natural products from 2000 to 2021. Each subsection focuses on the key strategic disconnections and the enantioselective steps controlling asymmetric induction.

scholarly journals Enantioselective Total Synthesis of Otteliones A and B, Novel and Powerful Antitumor Agents from the Freshwater Plant Ottelia alismoides

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Tadashi Katoh
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Anticancer Agents ◽  
Antitumor Agents ◽  
Formal Synthesis ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Significant Attention

Otteliones A and B isolated from the freshwater plant Ottelia alismoides have attracted significant attention because of their potential as novel anticancer agents. In this review four independent enantioselective total syntheses and one formal synthesis of these natural products are presented with particular focus on their methodology and strategy.

Unified enantioselective total synthesis of 3,6-dioxygenated diketopiperazine natural products, diatretol and lepistamides A, B and C

2021 ◽  
Vol 67 ◽  
pp. 152895
Author(s):  
Shu Takahashi ◽  
Aoi Kimishima ◽  
Tomoyasu Hirose ◽  
Takeshi Yamada ◽  
Akihiro Sugawara ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Enantioselective Total Synthesis

Total synthesis of the potent antifungal agents bengazole C and E

2009 ◽  
Vol 74 (6) ◽  
pp. 887-900 ◽  
Author(s):  
Álvaro Enríquez-García ◽  
Steven V. Ley
Keyword(s):  
Natural Products ◽  
Antifungal Activity ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Antifungal Agents ◽  
Nitrile Oxide ◽  
Total Syntheses ◽  
Unique Structure

The bengazoles are marine natural products with unique structure, containing two oxazole rings flanking a single carbon. They show very potent antifungal activity. The total syntheses of bengazole C and E are described following a convergent route which involves diastereoselective cycloaddition of an appropriately substituted nitrile oxide with a butane-1,2-diacetal-protected alkenediol as the key step.

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

Aryne-based strategy in the total synthesis of naturally occurring polycyclic compounds

2018 ◽  
Vol 47 (21) ◽  
pp. 8030-8056 ◽  
Author(s):  
Hiroshi Takikawa ◽  
Arata Nishii ◽  
Takahiro Sakai ◽  
Keisuke Suzuki
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Polycyclic Compounds ◽  
Total Syntheses ◽  
Naturally Occurring

This review has outlined the strategies and tactics of using arynes in the total syntheses of polycyclic natural products.

scholarly journals Contiguous Quaternary Carbons: A Selection of Total Syntheses

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3841
Author(s):  
Alina Eggert ◽  
Christoph Etling ◽  
Dennis Lübken ◽  
Marius Saxarra ◽  
Markus Kalesse
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Status Quo ◽  
Total Syntheses ◽  
The Status ◽  
Selection Of ◽  
Quaternary Carbons

Contiguous quaternary carbons in terpene natural products remain a major challenge in total synthesis. Synthetic strategies to overcome this challenge will be a pivotal prerequisite to the medicinal application of natural products and their analogs or derivatives. In this review, we cover syntheses of natural products that exhibit a dense assembly of quaternary carbons and whose syntheses were uncompleted until recently. While discussing their syntheses, we not only cover the most recent total syntheses but also provide an update on the status quo of modern syntheses of complex natural products. Herein, we review (±)-canataxpropellane, (+)-waihoensene, (–)-illisimonin A and (±)-11-O-debenzoyltashironin as prominent examples of natural products bearing contiguous quaternary carbons.

Construction of sulfur-containing moieties in the total synthesis of natural products

2020 ◽  
Vol 37 (2) ◽  
pp. 246-275 ◽  
Author(s):  
Nengzhong Wang ◽  
Puli Saidhareddy ◽  
Xuefeng Jiang
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Total Syntheses ◽  
Sulfur Containing

This review surveys the total syntheses of sulfur-containing natural products where sulfur atoms are introduced with different sulfurization agents to construct related sulfur-containing moieties.

Catalytic asymmetric dearomatization (CADA) reaction-enabled total synthesis of indole-based natural products

2019 ◽  
Vol 36 (11) ◽  
pp. 1589-1605 ◽  
Author(s):  
Chao Zheng ◽  
Shu-Li You
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Indole Derivatives ◽  
Total Syntheses ◽  
Catalytic Asymmetric

The recent enantioselective total syntheses of natural products enabled by catalytic asymmetric dearomatization reactions of indole derivatives are presented.

scholarly journals Total synthesis of the azolemycins

2016 ◽  
Vol 14 (4) ◽  
pp. 1450-1454 ◽  
Author(s):  
Zoe J. Anderson ◽  
David J. Fox
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Analogue ◽  
Total Syntheses

The first total syntheses of newly isolated polyazole natural products azolemycins A–D, along with the synthesis of the tetra-oxazole non-natural analogue, are described.

Sign in / Sign up

Export Citation Format

Share Document