Synthesis Of Heterocyclic Natural Products Research Articles

Synthesis of Natural Products by C-H Functionalization of Heterocycless.

Total synthesis is considered by many as the finest combination of art and science. During the last decades, several concepts were proposed for achieving the perfect vision of total synthesis, such as atom economy, step economy, or redox economy. In this context, C-H functionalization represents the most powerful platform that has emerged in the last years, empowering rapid synthesis of complex natural products and enabling diversification of bioactive scaffolds based on natural product architectures. In this review, we present an overview of the recent strategies towards the total synthesis of heterocyclic natural products enabled by C-H functionalization. Heterocycles represent the most common motifs in drug discovery and marketed drugs. The implementation of C-H functionalization of heterocycles enables novel tactics in the construction of core architectures, but also changes the logic design of retrosynthetic strategies and permits access to natural product scaffolds with novel and enhanced biological activities.

Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids.

Readily available 4-bromobenzo[c][2,7]naphthyridine undergoes regioselective direct ring metalation at C-5 with TMPMgCl∙LiCl at −40 °C. Quenching with various electrophiles gives a broad range of 5-substituted products, which are building blocks for the synthesis of heterocyclic natural products and analogues thereof. In combination with a Parham-type cyclization a novel approach to pyrido[4,3,2-mn]acridones has been worked out.

Cascade Reaction in the Synthesis of Heterocyclic Natural Products

Background: Cascade reactions, as an attractive branch of organic chemistry, have been the subject of intense research in the recent years. In these reactions numerous transformations occur in a single sequence, and the subsequent reactions are formed as a consequence of the functionality of the previous step. Cascade reactions are environmentally benign processes due to their one-pot procedure which accordingly proceed in a single reaction solvent, work-up, and purification step. Therefore, they are often associated with cost savings in terms of solvents, catalysts, and reagents in addition to time and effort. Keywords: Cascade reaction, tandem reaction, natural products, heterocycles, total synthesis, one-pot procedure.

New Developments in the Asymmetric Synthesis of Heterocyclic Natural Products

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Allenylzinc reagents: new trends and synthetic applications

The last developments in our research efforts involving allenylzinc reagents are summarized. These interesting organometallic compounds allow the stereoselective and enantioselective synthesis of acetylenic epoxides, aziridines and amino alcohols. Some synthetic applications of these highly functionalized substrates are also presented through the synthesis of homopropargylic alcohols and allenic ketones. Further applications in the total synthesis of heterocyclic natural products are also discussed.

New developments in the asymmetric synthesis of heterocyclic natural products

Various chiral α,β-unsaturated γ-lactams 1 were prepared in high yield and in a single step from corresponding primary amines. The different reactivities of lactams 1 could be exploited to prepare diversely substituted pyrrolidones, pyrrolidines, γ-aminoacids and alkaloids. Their application to the synthesis of enantiomerically pure (-)-cephalotaxine are described.

Recent progress in the synthesis of heterocyclic natural products by the Staudinger/intramolecular aza-Wittig reaction

A review of recent progress in the synthesis of heterocyclic natural products by the aza-Wittig method focusing on applications of the tandem Staudinger/intramolecular aza-Wittig reaction.

Recent Progress in the Synthesis of Heterocyclic Natural Products by the Staudinger/Intramolecular aza‐Wittig Reaction

AbstractFor Abstract see ChemInform Abstract in Full Text.

Domino Reactions in the Synthesis of Heterocyclic Natural Products and Analogues

AbstractFor Abstract see ChemInform Abstract in Full Text.

Domino reactions in the synthesis of heterocyclic natural products and analogs

Abstract Domino reactions are defined as processes of two or more bond-forming reactions under identical conditions, in which the subsequent transformation takes place at the functionalities obtained in the former transformation. They allow the efficient synthesis of complex molecules from simple substrates in an ecologically and economically favorable way. A very powerful domino process is the domino Knoevenagel–hetero-Diels–Alder reaction, in which an aldehyde or an beta-ketoester is condensed with a 1,3-dicarbonyl compound or a heteroanalog to give a 1-oxa-1,3-butadiene, which can undergo an inter- or intramolecular hetero-Diels–Alder reaction with dienophiles such as enol ethers or alkenes. The products are dihydropyrans, which can be transformed in a variety of ways. Thus, an extension of the process is the synthesis of highly substituted pyrrolidines, piperidines, and azepanes using aminoaldehydes. The process has also been employed for the enantioselective total synthesis of a variety of alkaloids, such as indol- and ipecacuanha alkaloids. In another domino process, erythrina and homoerythrina alkaloids have been prepared from simple phenylethylamines and ketoesters.

ChemInform Abstract: Synthesis of Heterocyclic Natural Products and Related Heterocycles by the Aza‐Wittig Methodology

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Synthesis of Heterocyclic Natural Products via Regio‐ and Stereocontrolled Palladium‐Catalyzed Reactions

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Strategies for the synthesis of heterocyclic natural products

Strategies for the synthesis of heterocyclic natural products

Synthesis of heterocyclic natural products: Model studies towards diazonamide A

Abstract

ChemInform Abstract: The Synthesis of Natural Heterocyclic Products by Hetero Diels‐Alder Cycloaddition Reactions

Publisher Summary This chapter highlights recent advances in the synthesis of natural products by hetero Diels– Alder cycloaddition reactions. These recent disclosures have a great impact on heterocyclic natural product syntheses. The Diels–Alder reaction is one of the most common and elegant methods for the construction of carbocyclic six-membered ring systems. Especially for the synthesis of polycyclic natural products, it presents an unrivaled opportunity for the regioselective and stereospecific introduction of multiple centers of configuration. This chapter also discusses recent reviews of Diels–Alder reactions with heterodienes which contains one or two hetero atoms. The chapter describes the utility of inter- and intramolecular [4 + 21-cycloaddition reaction using heterodienophiles of heterodienes and focuses on the synthesis of heterocyclic natural products.

ChemInform Abstract: Total Synthesis of Heterocyclic Natural Products by Development of New Methodologies

Chemischer InformationsdienstVolume 17, Issue 19 Reviews ChemInform Abstract: Total Synthesis of Heterocyclic Natural Products by Development of New Methodologies T. KAMETANI, T. KAMETANISearch for more papers by this author T. KAMETANI, T. KAMETANISearch for more papers by this author First published: May 13, 1986 https://doi.org/10.1002/chin.198619353Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume17, Issue19May 13, 1986 RelatedInformation

Synthesis of Heterocyclic Natural Products through Organoselenium Intermediates

Synthesis of Heterocyclic Natural Products through Organoselenium Intermediates

Total Synthesis of Heterocyclic Natural Products

Total Synthesis of Heterocyclic Natural Products