The Application of C-H bond Functionalization in Total Syntheses of Indole Natural Products

2022 ◽  
Author(s):  
Dong-Xing Tan ◽  
Fu-She Han
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Total Syntheses ◽  
Bond Functionalization ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
Direct Functionalization

The direct functionalization of unactivated C–H bonds is a rapidly growing field in organic chemistry in recent years because of its indisputable advantages in bond forming reactions in terms of...

Synthesis of natural products and analogs using multiple Pd-catalyzed transformations

2007 ◽  
Vol 79 (4) ◽  
pp. 629-650 ◽  
Author(s):  
Lutz F. Tietze ◽  
Tom Kinzel
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Vitamin E ◽  
Relative Stability ◽  
Chiral Ligands ◽  
Heck Reactions ◽  
Vast Number ◽  
Total Syntheses ◽  
Bond Forming ◽  
Palladium Catalyzed

Palladium-catalyzed transformations are of great importance in modern synthetic organic chemistry. The vast number of reactions that can be catalyzed by Pd0- as well as Pd2+-complexes in combination with the relative stability of the intermediates offers the intriguing opportunity of carrying out multiple consecutive bond-forming processes. They can be even performed in a domino fashion and in the presence of chiral ligands to allow the efficient preparation of almost enantiopure compounds. In this article, the use of double Heck, Tsuji-Trost-Heck, and Wacker-Heck reactions for the total syntheses of estradiol, spinosyn A analogs, cephalotaxine, and vitamin E is described.

scholarly journals Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 249
Author(s):  
Raquel G. Soengas ◽  
Humberto Rodríguez-Solla
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Functional Group ◽  
Biological Activities ◽  
Synthetic Methods ◽  
Bond Forming ◽  
Drug Candidates ◽  
The Past ◽  
Wide Range

The 1,3-butadiene motif is widely found in many natural products and drug candidates with relevant biological activities. Moreover, dienes are important targets for synthetic chemists, due to their ability to give access to a wide range of functional group transformations, including a broad range of C-C bond-forming processes. Therefore, the stereoselective preparation of dienes have attracted much attention over the past decades, and the search for new synthetic protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged in the last decade, with a focus on the synthetic processes that meet the requirements of efficiency and sustainability of modern organic chemistry.

scholarly journals Recent applications of imines as key intermediates in the synthesis of alkaloids and novel nitrogen heterocycles

2009 ◽  
Vol 81 (2) ◽  
pp. 195-204 ◽  
Author(s):  
Stephen F. Martin
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Multicomponent Reactions ◽  
Nitrogen Heterocycles ◽  
Biologically Active ◽  
Total Syntheses ◽  
Biological Interest ◽  
Cascade Processes ◽  
Novel Applications ◽  
Active Natural

One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions (MCRs) to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (±)-epilupinine (1), (±)-tashiromine (2), (-)-epimyrtine (3), and (±)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

scholarly journals Total syntheses of natural products containing spirocarbocycles

2015 ◽  
Vol 13 (39) ◽  
pp. 9907-9933 ◽  
Author(s):  
Laura K. Smith ◽  
Ian R. Baxendale
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Total Syntheses

The spiro motif is becoming an increasingly prevalent structure in medicinal and organic chemistry. The total syntheses of natural products containing all-carbon spirocycles is reviewed.

scholarly journals Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

2014 ◽  
Vol 10 ◽  
pp. 1848-1877 ◽  
Author(s):  
Thilo Focken ◽  
Stephen Hanessian
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Bioactive Compounds ◽  
Biologically Active ◽  
Bond Forming ◽  
Michael Additions ◽  
Bond Forming Reactions ◽  
Asymmetric Alkylations

A review of the synthesis of natural products and bioactive compounds adopting phosphonamide anion technology is presented highlighting the utility of phosphonamide reagents in stereocontrolled bond-forming reactions. Methodologies utilizing phosphonamide anions in asymmetric alkylations, Michael additions, olefinations, and cyclopropanations will be summarized, as well as an overview of the synthesis of the employed phosphonamide reagents.

scholarly journals Recent Chemical Methodology Advances in the Total Synthesis of Meroterpenoids

2021 ◽  
Vol 68 (2) ◽  
pp. 247-267
Author(s):  
Jan Petrovčič ◽  
Chad Nicholas Ungarean ◽  
David Sarlah
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Total Synthesis ◽  
Feature Article ◽  
Total Syntheses ◽  
Synthetic Organic Chemistry ◽  
Synthetic Studies

Heterogeneity of meroterpenoids arising from their dual biosynthetic origins is constantly provoking synthetic chemists to utilize their ingenuity and revise their retrosynthetic logic. By studying recent publications on meroterpenoid synthesis,tremendous advances in the field of synthetic organic chemistry can be witnessed. This feature article covers some of the most intriguing total syntheses and synthetic studies towards the meroterpenoid class of natural products from the last five years.

scholarly journals Concise total syntheses of (–)-jorunnamycin A and (–)-jorumycin enabled by asymmetric catalysis

Science ◽  
2018 ◽  
Vol 363 (6424) ◽  
pp. 270-275 ◽  
Author(s):  
Eric R. Welin ◽  
Aurapat Ngamnithiporn ◽  
Max Klatte ◽  
Guillaume Lapointe ◽  
Gerit M. Pototschnig ◽  
...  
Keyword(s):  
Natural Products ◽  
Asymmetric Catalysis ◽  
High Efficiency ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Polycyclic Compounds ◽  
Gram Negative ◽  
Total Syntheses ◽  
Bond Forming ◽  
The Past

The bis-tetrahydroisoquinoline (bis-THIQ) natural products have been studied intensively over the past four decades for their exceptionally potent anticancer activity, in addition to strong Gram-positive and Gram-negative antibiotic character. Synthetic strategies toward these complex polycyclic compounds have relied heavily on electrophilic aromatic chemistry, such as the Pictet–Spengler reaction, that mimics their biosynthetic pathways. Herein, we report an approach to two bis-THIQ natural products, jorunnamycin A and jorumycin, that instead harnesses the power of modern transition-metal catalysis for the three major bond-forming events and proceeds with high efficiency (15 and 16 steps, respectively). By breaking from biomimicry, this strategy allows for the preparation of a more diverse set of nonnatural analogs.

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